Herbicidal sulfonamides

ABSTRACT

This invention relates to novel herbicidally active sulfonylurea compounds substituted in the positions ortho to the sulfonylurea bridge, agriculturally suitable compositions thereof and methods of their use as preemergent or postemergent herbicides or plant growth regulants.

RELATED APPLICATION

This is a division of application Ser. No. 628,259, filed July 12, 1984U.S. Pat. No. 4,604,131, which is a continuation-in-part of U.S. Ser.No. 520,801 filed Aug. 5, 1983, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to novel herbicidal sulfonamide compounds withsubstituents in both positions ortho to the sulfonylurea bridge,suitable agricultural compositions thereof and a method for their use aspreemergent or postemergent herbicides or plant growth regulants.

Herbicidal sulfonamides of the type described herein are generallyreferred to in the art as "sulfonylurea" herbicides.

The "sulfonylurea" herbicides are an extremely potent class ofherbicides discovered within the last few years. This class ofherbicides, generally consists of a sulfonylurea bridge, --SO₂ NHCONH--,linking two aromatic or heteroaromatic rings. See, for example, thecompounds disclosed in U.S. Pat. Nos. 4,169,719, 4,127,405, 4,120,691,4,221,585, 4,190,432, 4,225,337, 4,371,391, 4,339,266, 4,191,553,4,305,884, 4,214,890, 4,339,267, 4,302,241, 4,342,587, 4,310,346,4,293,330, 4,301,286, 4,370,479, 4,370,480, 4,368,067, 4,369,320,4,348,219, 4,348,220, 4,333,760, 4,368,069, and 3,323,611 as well asEuropean Patent Application No. 79300982.0 (Publication No. 7,687,published Feb. 6, 1980).

New compounds effective for controlling the growth of undesiredvegetation are in constant demand. In the most common situation, suchcompounds are sought to selectively control the growth of undesiredvegetation to permit the growth of useful crops such as cotton, rice,corn, wheat and soybeans, to name a few. Unchecked weed growth in suchuseful crops can cause significant losses, reducing profit to the farmerand increasing costs to the consumer. In other situations, herbicidesare desired which will control all plant growth. Examples of areas inwhich complete control of all vegetation is desired are areas aroundfuel storage tanks, ammunition depots and industrial storage areas.There are many products commercially available for these purposes, butthe search continues for products which are more effective, less costlyand environmentally safe.

EPO Pub. No. 7,687, discloses herbicidal sulfonylureas bearingortho-carboxylic acid ester groups.

EPO Pub. No. 23,141, discloses herbicidal sulfonylureas bearingortho-sulfamoyl groups.

EPO Pub. No. 44,211, discloses herbicidal sulfonylureas bearingortho-phenyl groups.

EPO Pub. No. 44,209, discloses herbicidal sulfonylureas bearing --CH₂ ORand CH₂ CO₂ R₈ ortho-groups.

EPO Pub. No. 35,893, discloses herbicidal sulfonylureas bearing anortho-sulfonyl group.

EPO Pub. No. 44,212, discloses herbicidal sulfonylureas bearingortho-sulfonate groups.

U.S. Pat. No. 4,369,058, issued Jan. 18, 1983 discloses herbicidalsulfonylureas bearing ortho-amino substituents.

EPO Pub. No. 83,975, discloses herbicidal sulfonylureas bearingortho-heterocyclic substituents.

EPO Pub. No. 85,476, discloses herbicidal sulfonylureas bearingortho-pyridyl, pyrimidyl, triazinyl and furanyl groups.

South African Patent Application No. 83/0127 discloses herbicidalN-arylsulfonyl-N'-pyrimidinylureas of formula ##STR1## where X isoptionally substituted phenyl or naphthyl.

South African Patent Application No. 83/0441 discloses herbicidal ureasof formula ##STR2## where X is O, S, SO or SO₂ ;

m is 0 or 1; and

Q is any of a wide variety of moieties.

South African Patent Application No. 83/8416 discloses herbicidalsulfonamides of formula ##STR3## where A is an unsaturated or onlypartially saturated 5- or 6-membered heterocyclic ring system which isbonded through a carbon atom and contains 1, 2 or 3 heteroatoms andwhich may be substituted; and

R₁ is H, halo, NO₂, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁-C₄ haloalkoxy, C₁ -C₄ alkoxycarbonyl, C₁ -C₄ alkylthio, C₁ -C₄alkylsulfinyl, C₁ -C₄ alkylsulfonyl or C₂ -C₅ alkoxyalkoxy.

SUMMARY OF THE INVENTION

Novel compounds, suitable agricultural compositions thereof and a methodfor their use as preemergent or postemergent herbicides or plant growthregulants have been found. The novel compounds of this invention are ofthe formula ##STR4## wherein R₁ is S(O)_(n) R₅, CF₃, NR₆ R₇, CO₂ R₈, SO₂NR₉ R₁₀, ##STR5## OSO₂ R₁₃, CH₂ OR₁₄ or Q; R₂ is S(O)_(m) R₅, CF₃, NR₆R₇, CO₂ R₈, SO₂ NR₉ R₁₀, ##STR6## OSO₂ R₁₃, CH₂ OR₁₄ or Q; R₃ is H, Cl,F, Br, CH₃, OCH₃ or CF₃ ;

R₄ is H or CH₃ ;

R₅ is C₁ -C₃ alkyl;

R₆ and R₇ are independently CH₃ or CH₂ CH₃ ;

R₈ is C₁ -C₃ alkyl, CH₂ CH═CH₂, CH₂ CH₂ Cl or CH₂ CH₂ OCH₃ ;

R₉ is CH₃ or OCH₃ ;

R₁₀ is C₁ -C₃ alkyl;

R₁₁ is H, Cl, Br, F, CH₃ or OCH₃ ;

R₁₂ is H or CH₃ ;

R₁₃ is C₁ -C₃ alkyl or CF₃ ;

R₁₄ is C₁ -C₃ alkyl or CF₂ H;

n is 0, 1 or 2;

m is 0 or 1; ##STR7## W is O, S or NR₁₈ ; W' is O or S;

R₁₅, R₁₆, R₁₇ and R₁₈ are independently H or CH₃ ;

Q is also ##STR8## R₁₉, R₂₀, R₂₂, R₂₄ and R₂₅ are independently H or CH₃;

R₂₁ and R₂₃ are independently H, CH₃ or OCH₃ ;

Q is also ##STR9## R₂₆, R₂₇, R₂₈, R₂₉, R₃₀ and R₃₁ are independently Hor CH₃ ; ##STR10## Z is CH or N; L is O or CH₂ ;

X is CH₃, OCH₃, Cl, OCH₂ CH₃, or OCF₂ H or F;

Y is H, NH₂, NHCH₃, N(CH₃)₂, CH₃, CH₂ CH₃, CF₃, CH₂ OCH₃, CH₂ OCH₂ CH₃,O(C₁ -C₃ alkyl), SCH₃, O(C₃ -C₄ alkenyl), O(C₃ -C₄ alkynyl), OCH₂ CF₃,OCH₂ CH₂ F, OCH₂ CH₂ Cl, OCH₂ CH₂ Br or OCF₂ H;

X₁ is CH₃, OCH₃, Cl or OCF₂ H;

Y₁ is CH₃ or OCH₃ ;

X₂ is CH₃, CH₂ CH₃ or CH₂ CF₃ ;

Y₂ is CH₃, OCH₃ or SCH₃ ; and

Y₃ is H or CH₃ ;

and agriculturally suitable salts thereof;

provided that

(a) when either one of R₁ or R₂ is CF₃, then the other is also CF₃ ;

(b) R₁ and R₂ are not simultaneously CO₂ R₈ ;

(c) when either one of R₁ or R₂ is SO₂ NR₉ R₁₀, then the other must notbe S(O)_(n) R₅, S(O)_(m) R₅, CH₂ OR₁₄ or NR₆ R₇ ;

(d) when R₉ is OCH₃, then R₁₀ is CH₃ ;

(e) when either one of R₁ or R₂ is CO₂ R₈, then the other must not beS(O)_(n) R₅, S(O)_(m) R₅ or NR₆ R₇ ;

(f) the total number of carbon atoms in R₂₆ to R₃₁ combined, is equal toor less than four;

(g) when X is Cl or F, then Z is CH and Y is NH₂, NHCH₃, N(CH₃)₂, OCH₃or OCH₂ CH₃ ;

(h) when R₁ is CO₂ R₈ and R₂ is OSO₂ R₁₃, then A is not A-1; and

(i) when X or Y is OCF₂ H and A is A-1, then R₂ is Q.

The preferred compounds of the invention for their higher herbicidalactivity, greater plant growth regulant activity and/or more favorableease of synthesis are:

(1) Compounds of Formula 1 where A is A-1; R₁ and R₂ are notsimultaneously Q and R₄ is H.

(2) Compounds of Preferred 1 where Y is CH₃, CF₃, CH₂ OCH₃, OCH₃, OCH₂CF₃ or OCF₂ H.

(3) Compounds of Preferred 2 where R₃ is in either the 3- or 5-position.

(4) Compounds of Preferred 3 where R₁ and R₂ are not simultaneously SO₂NR₉ R₁₀ or NR₆ R₇.

(5) Compounds of Preferred 4 where R₃ is H; and at least one of R₁ or R₂is S(O)_(n) R₅, S(O)_(m) R₅, CF₃, NR₆ R₇, SO₂ NR₉ R₁₀, ##STR11## OSO₂R₁₃ or CH₂ OR₁₄. (6) Compounds of Preferred 5 where R₅ is CH₃ or CH₂ CH₃; R₆ and R₇ are both CH₃ ; R₁₀ is CH₃ ; R₁₁ is H; R₁₃ is CH₃ or CH₂ CH₃; and R₁₄ is CH₃.

(7) Compounds of Preferred 6 where X is CH₃, OCH₃ or Cl and Y is CH₃,OCH₃ or CH₂ OCH₃.

The most preferred compounds of the invention for their highestherbicidal activity, greatest plant growth regulating activity and/ormore favorable ease of synthesis are:N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide,andN-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,6-bis(methylthio)benzenesulfonamide.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The compounds of Formula (I) may be prepared by one or more of themethods described below in Equations 1 to 4. The method of choicedepends on the acid or base lability of the substituents and would beobvious to one skilled in the art.

As shown in Equation 1 below, compounds of Formula I can be prepared bythe reaction of an appropriately substituted sulfonamide of Formula (II)with the appropriate methyl carbamate of Formula (III) in the presenceof an equimolar amount of trimethylaluminum. The reactions are bestcarried out at 25° to 85° in an inert solvent such as methylene chlorideor 1,2-dichloroethane under an inert atmosphere.

Equation 1 ##STR12## where R₁ or R₂ is not CO₂ R₈ ;

R₃ =H, Cl, F, Br, CH₃, OCH₃ or CF₃ ; and R₄ is H.

Compounds of Formula (I) can also be prepared by reactingsulfonylcarbamate of Formula (IV) with an appropriate amine of Formula(V) as shown in Equation 2. The reaction is carried out at 50° to 100°in a solvent such as dioxane for 0.5 to 24 hours as taught in EPOPublication No. 44807, published Jan. 27, 1982. The required carbamatesare prepared by reacting the preformed sodium salt of II withdiphenylcarbonate.

Equation 2 ##STR13## wherein R₁ or R₂ is S(O)_(n) R₅, CF₃, NR₆ R₇, SO₂NR₉ R₁₀, C₆ H₄ R₁₁, CH₂ OR₁₄ or Q;

R₃ is as described in Equation 1; and

R₄ is H or CH₃.

Some of the compounds of Formula (I) can also be prepared as shown inEquations 3a and 3b.

Equation 3a ##STR14##

The reaction of Equation 3a can be carried out by contacting equimolaramounts of a sulfonamide of Formula (II) with a heterocyclic phenylcarbamate of Formula (VI) in the presence of an equimolar amount of1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), by methods analogous to thosedescribed in South African Patent Application No. 830441. The phenylcarbamates of Formula (VI) can be prepared by methods, or modificationsthereof known to those skilled in the art, described in South AfricanPatent Application No. 825671 and South African Patent Application No.825045.

Rarely a sulfonamide (II) may not be of sufficient stability to beuseful as a starting material in Equations 1-3a. In this case, as wellas others, the sulfonyl isocyanate (VIII), can be made as an unisolatedintermediate by treating the corresponding sulfonyl chloride (XV) withisocyanate anion in the presence of the heterocyclic amine (V). Theamine reacts with the sulfonyl isocyanate as it is formed to give thedesired compound of Formula I.

Equation 3b ##STR15##

The reaction is best carried out by adding over one to six hours asolution of at least one equivalent of a tetraalkylammonium isocyanate,such as tetra-n-butylammonium isocyanate, in a suitable aprotic organicsolvent, such as dichloromethane or tetrahydrofuran, to a well-stirredmixture of one equivalent of sulfonyl chloride (XV) and at least oneequivalent of heterocyclic amine (V) in a similar suitable organicsolvent at 20°-40° C. The reaction mixture is then diluted withdichloromethane, washed with 1N sulfuric acid, and dried over sodiumsulfate. Rotary evaporation of the solvent leaves the product of Formula(I).

The compounds of Formula I may be prepared as shown below in Equation 4by the reaction of an appropriate benzenesulfonyl isocyanate, VIII withan appropriate aminoheterocycle, V.

Equation 4 ##STR16## wherein R₁, R₂, R₃ and R₄ are as described inEquation 2; and

R₁ or R₂ may also be CO₂ R₈, ##STR17## and OSO₂ R₁₃.

The reaction of Equation 4 is best carried out in an inert aproticsolvent such as methylene chloride, tetrahydrofuran or acetonitrile at atemperature between 20° and 80°. A catalytic amount of1,4-diazabicyclo[2,2,2]octane (DABCO) may be used to accelerate thereaction. In cases in which the products are insoluble in the reactionsolvent, they may be isolated by simple filtration. When the productsare soluble, they may be isolated by evaporation of the solvent andtrituration of the residue with solvents such as 1-chlorobutane, diethylether or methanol and filtration. Impure products may be purified bycolumn chromatography on silica gel.

The benzenesulfonyl isocyanates of Formula (VIII) may be prepared asshown in Equation 5, by phosgenation of the sulfonamides (II) in thepresence of butyl isocyanate.

Equation 5 ##STR18## wherein R₁, R₂ and R₃ are as described in Equation4.

The above reaction is carried out by heating a mixture of theappropriate sulfonamide (II), an alkyl isocyanate such as butylisocyanate and a catalytic amount of a tertiary amine such as1,4-diazabicyclo[2,2,2]octane (DABCO) in xylene, or other inert solventof boiling point ≧135°, to approximately 135°. Phosgene is then added tothe mixture over a 1-6 hour period at 125°-135° until an excess ofphosgene is present as indicated by a permanent drop in the boilingpoint to less than 130°. The mixture is cooled and filtered to remove asmall amount of insoluble by-products. The solvent and the alkylisocyanate are distilled off in vacuo leaving a residue of the crude,sulfonyl isocyanate (VIII) which can be used without furtherpurification. This method is described in U.S. Pat. No. 4,238,621.

Alternatively, the sulfonyl isocyanates (VIII) can be prepared, as shownin Equation 6, in a two-step procedure. This method is similar to aprocedure taught by Ulrich and Sayigh, New Methods of PreparativeOrganic Chemistry, Vol. VI, p. 223-241, Academic Press, New York andLondon, W. Forest Ed.

Equation 6 ##STR19## wherein R₁, R₂ and R₃ are as described in Equation4.

The compounds of Formula (IX) are conveniently prepared by stirring amixture of sulfonamides (II) anhydrous potassium carbonate, and n-butylisocyanate in a solvent such as acetone or methyl ethyl ketone at25°-80° until all of the isocyanate has reacted. The products areisolated by quenching in dilute mineral acid and recrystallizing thesolid product. The compounds (IX) are treated with phosgene and acatalytic amount of DABCO in refluxing xylene or chlorobenzene in amanner analogous to that described in Equation 5.

Sulfonyl isocyanates of Formula (VIII) may also be prepared by theprocedure shown below in Equation 7 starting from the appropriatesulfonamides.

Equation 7 ##STR20## wherein R₁, R₂ and R₃ are as described in Equation2.

The reactions of Equation 7 are best carried out according to theprocedure of Ulrich et al. in J. Org. Chem., 34, 3200 (1969). Thesulfonamide is boiled under reflux with an excess of thionyl chloridewhich functions as both a reactant and solvent. When the sulfonamideprotons are no longer detectable by proton NMR (15-20 hrs. on theaverage), the thionyl chloride is removed under reduced pressure and theresidue is dissolved in an inert solvent such as toluene, benzene,xylenes, etc. A catalytic amount of pyridine is added. The mixture istreated with at least one equivalent of phosgene and heated to 60°-140°with 80°-100° C. preferred. Conversion to the isocyanate issubstantially complete within about 1/4 to 3 hours. The mixturecontaining the sulfonyl isocyanate can be used directly or the sulfonylisocyanate can be isolated in pure form by filtration and evaporation ofthe filtrate followed by vacuum distillation if necessary.

As shown in Equation 8 below, intermediate sulfonamides for Formula (II)can be prepared from t-butyl sulfonamides (XI). Of necessity, thereactions are limited to those cases in which R₁ is inert to lithiumreagents under the conditions employed. During metallation, acids can beprotected as amides and alcohols protected as tetrahydropyran ethers.For a general review of metallation with lithium reagents, see H. W.Gschwend and R. Rodriguez, Org. Reactions, 26, 1 (1979).

Equation 8 ##STR21## where R₁ is not CH₂ CO₂ R₈, CO₂ R₈, OSO₂ R₁₃ or CH₂OR₁₄ ; ##STR22## where R₁ is as defined above;

E is R₅ SSR₅, CO₂, ##STR23## CH₂ O, CH₃ I, or CH₃ CH₂ I; and R₂ is SR₅,CO₂ H, CO₂ R₈, CH₂ OH, CH₃ or CH₂ CH₃. ##STR24## where R₁ is as definedabove. ##STR25## where R₁ is as defined above; and

R₂ is C₆ H₄ R₁₁ or Q. ##STR26## where R₁ is SR₅, CF₃, NR₆ R₇, CO₂N(CH₃)₂, SO₂ NR₉ R₁₀, C₆ H₄ R₁₁, OH, CH₂ OH, Q or ##STR27## R₂ is SR₅,CO₂ H, CO₂ R₈ or CH₂ OH; and R₃ is as defined in Equation 2.

Reaction step (8a) is best carried out under nitrogen in an inertanhydrous aprotic solvent such as tetrahydrofuran, diethyl ether orhexane at temperatures between -78° and 40° C. in a manner similar tothat of J. G. Lombardino [J. Org. Chem., 36, 1843 (1971)].

The preferred mode of addition is to add at least two equivalents of thealkyllithium or phenyllithium reagent to a -45° solution of thesulfonamide (XI) in tetrahydrofuran. After 15 minutes to 3 hours at roomtemperature, the lithium salt XIIa is obtained.

In Equation 8b, the reaction mixture is cooled to between 0° to -78° anda disulfide, carbon dioxide, chloroformate, dialkyl carbonate,formaldehyde, methyl iodide or ethyl iodide added to the lithium salt.The mixture is then allowed to warm and is stirred at ambient to refluxtemperature for 6 to 20 hours. The addition of dilute acetic acid orammonium chloride removes inorganic salts from the product contained inthe organic phase to provide sulfonamides (XIIb).

In reaction 8c, XIIa is reacted with cuprous iodide at temperaturesbelow 0° C., presumably forming XIIc. After 10 minutes to 1 hour, thearyl iodide or heterocyclic iodide is added and the mixture heated atreflux for 12 to 24 hours. After quenching the reaction with a diluteacid such as hydrochloric acid, ammonium hydroxide can be added in thepresence of air to facilitate removal of the copper salts. The productmay be extracted with solvents such as ethyl acetate or ether. Theresidue may be purified by chromatography or triturated using solventssuch as hexane/chloroform or hexane/ether.

Several studies on the competition of substituents for ortho-directioncapabilities indicates that for substituted sulfonamides, lithiation isdirected to the position adjacent to the sulfonamide group:

D. W. Slocum and C. A. Jennings

J. Org. Chem., 41, 3653 (1976);

A. I. Meyers and K. Lutomski

J. Org. Chem., 44, 4464 (1979);

P. Beak and R. A. Brown

J. Org. Chem., 47, 34 (1982); and

P. Beak and V. Snieckus

Acc. Chem. Res., 15, 306 (1982).

For example, the metallation of (XIa) was found to occur in the6-position. The absence of metallation at the 3 position or on thethiomethyl group attests to the powerful directing influence of thesulfonamide group and the thermodynamic stability of the resultinganion. ##STR28##

Reaction step (8e) is best carried out in trifluoroacetic acid orethanolic hydrogen chloride between ambient and reflux temperatures for18 to 48 hours according to the method of J. G. Lombardino [J. Org.Chem., 36, 1843 (1971)].

The deprotection appears to be concentration dependent. The yield ofsulfonamide (II) can usually be increased by using a large excess of theacid as a solvent or by stripping off the by-products after 18 hours andredissolving or resuspending the residue in the acid of choice andstirring an additional 20 to 30 hours. The solvent is distilled off invacuo and the residue can be triturated and recrystallized with solventssuch as 1-chlorobutane or chloroform/hexane. The products can also bepurified by chromatography.

Some sulfonamides (XIIe) are best prepared from (XIb) in a "one pot"sequence, an example of which is shown in Equation 8f.

Equation 8f ##STR29## where R₅ and R₅ ' are independently C₁ -C₃ alkyl.

This reaction is best carried out in an inert atmosphere in an anhydrousaprotic solvent such as tetrahydrofuran, dimethylethylether or diethylether at temperatures between -78° and 40° C. in a manner similar tothat described for Equation 8a.

The method of choice is to treat a -45° C. solution of sulfonamide (XIb)in tetrahydrofuran sequentially with (1) 2.2 equivalents of alkyllithiumat -45° C. followed by warming to room temperature and stirring for 2hours, (2) 1.0 equivalent of dialkyl disulfide at 0° C. followed bywarming to ambient temperature and stirring for 2 hours, (3) 1.1equivalent of alkyllithium at -45° C. followed by warming to roomtemperature and stirring for 2 hours, and (4) 1.2 equivalents of dialkyldisulfide at 0° C. followed by stirring at ambient temperature for 18hours.

The sulfonamides of Formula (XIIg) can be prepared from compounds ofFormula (XIIf) as shown in Equation 8g.

Equation 8g ##STR30## wherein R₁ and R₃ are as described in Equation 8a;

R₁₂ is H or CH₃ ; and

R₈ is H, CH₃, CH₂ CH₃ or CH₂ CH₂ CH₃.

The above reaction is best carried out at -45° to 0° under conditionsdescribed for Equations 8a and b. The lithiation ofo-toluenesulfionamides and their subsequent reactions is described by H.Watanabe and C. R. Hauser [J. Org. Chem., 33, 4278 (1968)].

The sulfonamides of Formula (XIIf) can be prepared as described inEquation 8b.

Many sulfonamides of Formula (XI) can be prepared from the correspondingsulfonyl chlorides in a manner similar to that taught by J. G.Lombardino [J. Org. Chem., 36, 1843 (1971)] as shown below.

Equation 8h ##STR31## wherein R₁ and R₃ are as defined in Equation 2.

The reaction of Equation 8h is accomplished by treating a 0° C. solutionof at least two equivalents of t-butyl amine in a solvent such aschloroform with the sulfonyl chloride (XIII). The temperature is kept at0° to 15° C. for 1 hour then raised to 50° to 80° C. and held at thattemperature for 1 to 3 hours. This mixture is then poured into cold acidsuch as hydrochloric acid and extracted into a solvent such as methylenechloride or ethyl ether. Products are isolated by evaporation of thesolvent and trituration of the solid residues with solvents such ashexane, chloroform or 1-chlorobutane.

The sulfonyl chlorides of Formula (XIII) have been disclosed. Certainsulfonyl chlorides are best prepared by chlorosulfonation of asubstituted benzene according to the teaching of H. T. Clarke et al.,Org. Synth. Coll. Vol. 1, 2nd Ed., 1941, p. 85. Other benzenesulfonylchlorides are best prepared by diazotization of the appropriate anilinewith sodium nitrite in HCl, followed by reaction of the diazonium saltwith sulfur dioxide and cuprous chloride in acetic acid according to theteaching of H. L. Yale and F. Sowinski, J. Org. Chem., 25, 1824 (1960).In addition, the oxidative chlorination of mercaptans to preparesulfonyl chlorides is widely reported in the literature, e.g., Gilbert,"Sulfonation and Related Reactions," pp. 202-214, IntersciencePublishers, New York, 1965.

Sulfonamides of Formula (II) can also be prepared using the two stepprocedure shown in Equation 9.

Equation 9 ##STR32## wherein R₁ or R₂ is CF₃, NR₆ R₇, SO₂ NR₉ R₁₀ or C₆H₄ R₁₁ ; and

R₃ is as defined in Equation 2. ##STR33## wherein R₁, R₂ and R₃ are asdefined above.

The reaction in Equation 9A is best carried out under nitrogen in ananhydrous, aprotic solvent such as tetrahydrofuran or diethyl ether withat least one equivalent of the alkyllithium at temperatures between-110° and -45° for 15 minutes to two hours. Sulfuryl chloride is thenadded and the mixture allowed to slowly warm to ambient temperature overthe 1 to 4 hours. An aqueous wash removes inorganic salts and theproduct is obtained after evaporation of the solvent in vacuo. The crudesulfonyl chloride XV can be used without further purification. Thereaction of sulfuryl chloride and phenyllithium is described by S. N.Bhattacharya et al. [J. Chem. Soc. C., 1265 (1968)].

The initial site of lithiation depends on the directing ability of thevarious substituents. During metallation, acids are protected as amidesand phenols are protected as tetrahydrofuran ethers. Benzyl alcohols maybe metallated by preparing the dianion as taught by D. Seebach [Agnew.Chem. Int. Ed. Engl. 17,521 (1978)]. In general, the highest degree oflithiation occurs between the more powerful directing groups. Thus, oneskilled in the art may determine which isomer will predominate.

For example, metallation at the 2-position of several 1,3-substitutedbenzenes has been reported: ##STR34##

The amination described in the reaction of Equation 9b is convenientlycarried out by treating a solution of the sulfonyl chloride with atleast two mole equivalents of anhydrous ammonia in a solvent such asethyl ether or methylene chloride at -20° to 30° C. If the sulfonamideproduct II is insoluble, it may be isolated by filtration followed bywashing out the salts with water. If product II is soluble in thereaction solution, it may be isolated by filtering off the precipitatedammonium chloride and evaporation of the solvent. Alternatively, manysulfonamides II can be prepared by reaction of corresponding sulfonylchlorides IX with excess aqueous ammonium hydroxide in tetrahydrofuranat 0° to about 40° C. for 0.5 to 10 hours. The sulfonamide product II isisolated by evaporation of the tetrahydrofuran solvent, addition ofwater to the residue and filtration.

In some cases the sulfonamides (II) are prepared from the sulfinic acidsalts (XVI). The procedure of Equation 9c is well known in the art. SeeU.S. Pat. No. 4,127,405 and Organic Reactions, Vol. 26, 1979, J. Wileyand Sons, Inc., N.Y. Sulfonamides (II) are best prepared by treatment ofsulfinic acid salts with chloramine. In this procedure an etherealsolution or suspension of the salt (XVI) is treated at low temperatures(25° to -30°) with a dry ethereal solution of chloramine. The reactionis stirred for a period of several minutes to several hours. Afterfiltration, the reaction mixture is washed with aqueous bisulfite andthen dried and the solvent removed on a rotary evaporator. The crudeproduct is further purified by usual methods such as crystallization orchromatography.

Equation 9c ##STR35## wherein R₁, R₂ and R₃ are as defined in Equation9a.

The sulfonamides (II) can be prepared from the corresponding nitrocompounds as shown in Equation 10.

Equation 10 ##STR36## wherein R₃ is as defined in Equation 2; and

R₁₃ is C₁ -C₃ alkyl or CF₃. ##STR37## wherein R₃ and R₁₃ are as definedabove. ##STR38## wherein R₃ and R₁₃ are as defined above.

Reaction step 10a is best carried out in a solvent which will also actas an acid scavenger such as pyridine at temperatures below 10° C.during the addition of methanesulfonyl chloride. After 2 to 20 hours atambient temperature, the products can be isolated by pouring the mixtureinto a cold solution of acid such as hydrochloric acid and washing theresulting precipitate with dilute acid.

The reduction in Equation 10b can be run by any of several methods inthe literature. For example, the reaction can be run using catalyticreduction with 10% palladium-on-charcoal in an inert solvent such asmethanol or tetrahydrofuran at 25° to 45° C. at 1 to 3 atmospheres ofhydrogen. For details refer to a similar procedure described by M.Vincent, et al., Bull. Soc. Chim. France, 1580 (1962).

The reaction of Equation 10c is accomplished by treating a solution ofamine such as (XIX) in a mixture of concentrated hydrochloric acid andglacial acetic acid with a solution of sodium nitrite in water at -5° to5° C. After stirring for 10-30 minutes at about 0° C. to insure completediazotization, the solution is added to a mixture of an excess of sulfurdioxide and a catalytic amount of cuprous chloride or cupric chloride inglacial acetic acid at about 10° C. The temperature is kept at about 10°C. for 1/4 to 1 hour, then raised to 20° to 30° C. and held at thattemperature for 2 to about 24 hours. This solution is then poured into alarge excess of ice water. The sulfonyl chloride XV can be isolated byfiltration or by extraction into a solvent such as ethyl ether,methylene chloride or preferably, 1-chlorobutane, followed byevaporation of the solvent.

The amination is conveniently carried out as described for Equation 9bto provide sulfonamide (IIa).

Several heterocyclic sulfonamides (II) are conveniently prepared fromthe 2,6-disubstituted nitro compounds which are commercially availableor described in Beilstein: for example, 2,6-dimethyl nitrobenzene;2-nitro-3-methyl benzoic acid; and 2-nitro-3-methyl benzaldehyde.

The heterocyclic amines of Formula (V) in Equations 1a and 3 are alsoimportant intermediates for the preparation of the compounds of thisinvention, which can be prepared by the following methods.

The pyrimidines and triazines of Formula (Va) to (Vd) below are eitherknown or can be prepared by obvious methods by one skilled in the art.For instance, the synthesis of pyrimidines and triazines of the generalformula (Va) has been reviewed in "The Chemistry of HeterocyclicCompounds", a series published by Interscience Publishers, Inc., NewYork and London. 2-Aminopyrimidines are described by D. J. Brown in "ThePyrimidines", Vol. 16 of this series. 2-Amino-1,3,5-triazines arereviewed by E. M. Smolin and L. Rapaport in "s-Triazines andDerivatives", Vol. 13 of the same series. The synthesis of triazines isalso described by F. C. Schaefer, U.S. Pat. No. 3,154,547 and by K. R.Huffman and F. C. Schaefer, J. Org. Chem., 28, 1812 (1963). Thesynthesis of the bicyclic amines (Vc) and (Vd) are described in EPOPublication No. 15,683, and that of (Vb) in European Patent PublicationNo. 46,677. ##STR39## wherein L, X, X₁, Y and Z are as originallydefined.

Heating equimolar amounts of ethyl propionimidate hydrochloride andN-aminoquanidine nitrate in pyridine gives 3-amino-5-ethyltriazole;German Pat. No. 1,073,499 (1960); Berichte, 96, 1064 (1963). ##STR40##Condensation of hydrazine with ethyl N-cyanoacetimidate yields3-amino-5-methyltriazole; Journal of Organic Chemistry, 28, 1816 (1963).##STR41## British Pat. No. 736,568 (1955) describes the synthesis of3-amino-5-mercaptotriazole. ##STR42## Condensing hydrazine with dimethylcyanodithioimidocarbonate in acetonitrile gives3-amino-5-methylthio-1,2,4-triazole while reaction of hydrazine withdimethyl N-cyanoimidocarbonate produces3-amino-5-methoxy-1,2,4-triazole; Journal of Organic Chemistry, 39, 1522(1974). ##STR43##

Reaction of substituted hydrazines with N-cyanothioimidocarbonates(prepared according to the procedure given in D. M. Wieland, Ph.D.Thesis, 1971, pp. 123-124) yields disubstituted aminotriazoles as shownbelow. ##STR44##

Many of the aminoheterocyclic intermediates of Formula (V) where R₄ ismethyl may be prepared by a two-step procedure as described for (VI) inEquation 11.

Equation 11 ##STR45## wherein X, Y and Z are as originally defined and

R₄ is CH₃.

A solution of the amine (XX) in concentrated hydrochloric acid istreated with sodium nitrite solution and the chloro compound (XXI) isisolated in the usual manner by filtration of the acidic solution. Arepresentative procedure is described by Bee and Rose in J. Chem. Soc.C, 2031 (1966), for the case in which Z=CH, and X=Y=OCH₃. Displacementof the chlorine of (XXI) may be accomplished by heating with an excessof methylamine in water to obtain the methylamino heterocycle (VI).

Equation 12 below illustrates the preparation of the required methylpyrimidinyl carbamates and methyl triazinyl carbamates of Formula (III)in Equation 1. By obvious modifications, other methyl carbamates ofFormula (III) may be prepared by this method by one skilled in the art.

Equation 12 ##STR46## wherein X, Y and Z are as originally defined; and

R₄ is H.

According to Equation 12, a heterocyclic amine is reacted with twoequivalents of sodium hydride and excess dimethyl carbonate to formIIIa. The reaction is run in an inert solvent such as tetrahydrofuran at25° C. to reflux for 1 to 24 hours. The product is isolated by (a)adding about two equivalents of concentrated hydrochloric acid undernitrogen at 0° to 30° C.; (b) filtering; and (c) separating out theorganic phase, then drying (sodium sulfate and/or magnesium sulfate) andconcentrating to dryness in vacuo. The product IIIa may be purifiedfurther by recrystallization or chromatography procedures.

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by treating compounds of Formula I witha solution of alkali or alkaline earth metal salt having a sufficientlybasic anion (e.g., hydroxide, alkoxide, carbonate or hydride).Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of onecation to another. Cationic exchange can be effected by direct treatmentof an aqueous solution of a salt of a compound of Formula I (e.g.,alkali metal or quaternary amine salt) with a solution containing thecation to be exchanged. This method is most effective when the desiredsalt containing the exchanged cation is insoluble in water, e.g., acopper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I (e.g., an alkali metal or quaternary aminesalt) through a column packed with a cation exchange resin containingthe cation to be exchanged. In this method, the cation of the resin isexchanged for that of the original salt and the desired product iseluted from the column. This method is particularly useful when thedesired salt is water-soluble, e.g., a potassium, sodium or calciumsalt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is furtherillustrated by the following specific examples. Unless otherwiseindicated, temperatures are in degrees centigrade.

EXAMPLE 1 N-[1,1-(Dimethylethyl)]-2-(methylthio)benzenesulfonamide (XIa;R₁ =SCH₃, R₃ =H)

To a mixture of 21.3 g (0.10 mol) ofN-[1,1-(dimethylethyl)]benzenesulfonamide in 400 ml anhydroustetrahydrofuran (THF) under nitrogen atmosphere was added 137 ml (0.22mol) 1.6M butyllithium in hexanes dropwise at -40°. The mixture was thenwarmed to room temperature for 2 hours then recooled to -20° and treatedwith 10.8 ml (0.12 mol) methyl disulfide in 15 ml THF. After stirringovernight at ambient temperature, 80 ml of 10% hydrochloric acid wasadded and the layers separated. The aqueous phase was extracted withether and the combined organic extracts washed with brine, dried, andevaporated to a solid. The residue was triturated with ether/hexanes andcollected to afford 23.5 g of the title compound, m.p. 138°-140°.

NMR (CDCl₃): δ 1.20 (s, 9H); 2.58 (s, 3H); 5.39 (s, NH); 7.2-7.6 (m,4H); and 8.02-8.27 (m, 1H) ppm.

EXAMPLE 2N-(1,1-Dimethylethyl)-2-(methylthio)-6-phenylbenzenesulfonamide (XIId;R₁ =SCH₃, R₂ =C₆ H₅, R₃ =H)

A solution of 11.3 g (0.0436 mol)N-(1,1-dimethylethyl)-2-(methylthio)benzenesulfonamide in 300 mltetrahydrofuran (THF) was treated with 60.5 ml (0.0976 mol) 2Mn-butyllithium in hexanes at -30° under a nitrogen atmosphere. Themixture was stirred for 1 hour at ambient temperature then recooled to-20° and treated with 8.3 g (0.0436 mol) of cuprous iodide (anhydrous).After 10 minutes at -15°, 4.9 ml (0.0438 mol) iodobenzene was added andthe mixture was then heated to reflux overnight. Acetic acid (10 ml) wasadded after cooling the mixture to 15°, then 200 ml concentratedammonium hydroxide plus 200 ml ethyl acetate was introduced and themixture was stirred vigorously in the presence of air to facilitateremoval of the copper salts. The aqueous phase was separated, extractedwith more ethyl acetate and the combined organic extracts were washedsuccessively with concentrated ammonium hydroxide, water and brine, thendried (MgSO₄) and evaporated to an oil. The product crystallized fromether/hexanes to afford 10 g of material, m.p. 162°-165°.

NMR (CDCl₃): δ 1.1 (s, 9H); 2.65 (s, 3H); 5.2 (s, NH); 7.2 (t, J=4 Hz,1H); and 7.5 (m, 7H) ppm.

EXAMPLE 3 2,6-Bis(methylthio)-N-(1,1-dimethylethyl)benzenesulfonamide(XIIb; R₁ =R₂ =SCH₃, R₃ =H)

Under nitrogen, a homogeneous solution of 80 g ofN-(1,1-dimethylethyl)benzenesulfonamide in 1100 ml dry THF was cooled to-40° and 516 ml of 1.6M n-butyllithium added dropwise at thistemperature. After the addition was complete, the reaction mixture wasallowed to warm to room temperature and stirred for 2 hours. Theresulting thick ppt. was cooled to 0° and 38 ml of methyl disulfideadded dropwise. After warming to room temperature, the suspension wasstirred for 1.5 hour. It was then cooled to -40° and an additional 285ml n-butyllithium added dropwise. The suspension was allowed to warm to25° C. and stirred at this temperature for 2 hours. Cooling to 0° andthe dropwise addition of 41 ml of methyl disulfide gave a bright orangesuspension. After stirring at room temperature for 18 hours, the whitesuspension was cooled to 0° and 20 ml of saturated ammonium chlorideadded dropwise. The mixture was poured into 1 l of water and extractedwith ether. An insoluble precipitate remained which was collected byfiltration and air dried to provide 42.3 g of2,6-bis(methylthio)-N-(1,1-dimethylethyl)benzenesulfonamide as a whitepowder, m.p. 182°-185°.

The combined ether extracts were washed twice with water, once withbrine and dried over sodium sulfate. Concentration gave a pale yellowsolid which was washed with n-butyl chloride, providing an additional34.5 g of the title compound, m.p. 174°-184°.

NMR (DMSO-d₆): δ 1.11 (s, 9, t-Bu); 2.48 (s, 6, SCH₃); and 7.12-7.65 (m,4).

IR (nujol): 3.05 (NH).

EXAMPLE 4 2-(Methylthio)-6-phenylbenzenesulfonamide (II; R₁ =SCH₃, R₂=C₆ H₅, R₃ =H)

In a mixture of 75 ml trifluoroacetic acid plus 2 ml water was dissolved10 g (0.030 mol) ofN-(1,1-dimethylethyl)-2-(methylthio)-6-phenylbenzenesulfonamide andheated to 85°. After 15 minutes the mixture was cooled and evaporated,then diluted with water and extracted with methylene chloride. Themethylene chloride was washed with saturated sodium bicarbonatesolution, dried (MgSO₄), evaporated in vacuo and crystallized fromether/hexanes to afford 6.5 g of the title compound, m.p. 167°-168°.

NMR (CDCl₃); δ 2.55 (s, 3H); 6.62 (2, NH₂); 7.07 (m, 1H); and 7.35-7.55(m, 7H) ppm.

EXAMPLE 5 2-(Methylsulfonyl)-6-phenylbenzenesulfonamide (II; R₁ =SO₂CH₃, R₂ =C₆ H₅, R₃ =H)

A solution of 6.5 g (0.023 mol)2-(methylthio)-6-phenylbenzenesulfonamide in 100 ml methylene chlorideplus 20 ml ethyl acetate was treated with 10 g (0.046 mol) 80%m-chloroperoxybenzoic acid. The mixture was subsequently stirred atambient temperature for 3 days then filtered. The solids were rinsedwith saturated sodium bicarbonate, water and more methylene chloride. Asecond crop was obtained from the combined bicarbonate washed methylenechloride filtrates to afford 6.9 g of the title compound, m.p.258°-259°.

NMR (CDCl₃ /DMSO-d₆): δ 3.50 (s, 3H); 6.95 (s, NH₂); 7.47 (s, 5H);7.5-7.98 (m, 3H); and 8.42 (m, 1H) ppm.

EXAMPLE 6N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-3-(methylsulfonyl)-1,1'-biphenyl-2-sulfonamide(I; R₁ =SO₂ CH₃, R₂ =C₆ H₅, R₃ =R₄ =H, A=A-1, X=OCH₃, Y=CH₃, Z=CH)

To a stirred suspension of 1.2 g (3.86 mmol)2-(methylsulfonyl)-6-phenylbenzenesulfonamide in 35 ml methylenechloride under nitrogen atmosphere was added 2.5 ml (5 mmol) of 2Mtrimethylaluminum in toluene via syringe at ambient temperature. Solidmethyl N-(4-methoxy-6-methylpyrimidin-2-yl)carbamate (0.95 g, 4.8 mmol)was then added and the mixture was heated to reflux for 1 day. Aqueous5% hydrochloric acid (50 ml) was added to the cooled mixture followed byether. The solid product which separated was collected and rinsed withether and water, then chromatographed on silica gel with 10% ethylacetate in methylene chloride as the eluant. Trituration of the solidproduct with ether/hexane afforded 0.32 g of the title compound, m.p.206°-208°.

NMR (CDCl₃ /DMSO-d₆): δ 2.30 (s, 3H); 3.60 (s, 3H); 3.88 (s, 3H); 6.27(s, 1H); 7.15-7.9 (m, 7H); 8.4 (sbr, NH); 8.45 (m, 1H); and 12.3 (sbr,NH) ppm.

IR (nujol); 1700, 3250 cm⁻¹.

EXAMPLE 7 2,6-Bis(methylthio)benzenesulfonamide (II; R₁ =R₂ =SCH₃ ; R₃=H)

A brown solution of 70 g of2,6-bis(methylthio)-N-(1,1-dimethylethyl)benzenesulfonamide in 200 mltrifluoroacetic acid was stirred at room temperature. After 10 minutes,a heavy precipitate formed, the suspension was stirred for 18 hours. Theresulting solid was collected by filtration and dissolved in 10% NaOH,filtered and the filtrate acidified with 10% HCl. The precipitated solidwas washed with water and air dried to provide 48 g of2,6-bis(methylthio)benzenesulfonamide, m.p. 197°-199°.

NMR (DMSO-d₆): δ 2.48 (s, 6, SCH₃); and 7.12-7.62 (m, 5).

IR (nujol); 2.90 and 3.00 (NH₂).

EXAMPLE 8 2,6-Bis(Methylthio)-N-(butylaminocarbonyl)benzenesulfonamide(IX; R₁ =R₂ =SCH, R₃ =H)

A stirred suspension of 5.0 g (0.02 mol) of2,6-bis(methylthio)benzenesulfonamide, 8.3 g (0.06 mol) potassiumcarbonate and 3.4 ml (0.03 mol) n-butyl isocyanate was heated at refluxfor four hours. After stirring at 25° C. overnight, the mixture waspoured into ice and 30 ml 10% HCl. The resulting precipitate wascollected, washed several times with water and air dried to provide 6.5g of the title compound, m.p. 151°-154°.

NMR (DMSO-d₆); δ 0.50-1.00 (m, 3); 1.00-1.47 (m, 4); 2.43 (s, 6);2.67-3.15 (m, 2); 6.18-6.56 (m, 1); and 7.10-7.75 (m, 3).

IR (nujol): 3.00 (NH); and 5.95 (c=o).

EXAMPLE 92,6-Bis(methylthio)-N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide(I; R₁ =R₂ =SCH₃, R₃ =H, A=A-1, X=Cl, Y=OCH₃, Z=CH)

A suspension of 2.3 g (6.7 mmol) of2,6-bis-(methylthio)-N-(butylaminocarbonyl)benzenesulfonamide and 0.07 g(0.67 mmol) of DABCO in 30 ml xylene was heated to 140°. To theresulting solution, phosgene (1.9 ml, 16 mmol) was added dropwise at135° to 140° C. The mixture was heated at reflux for 2 hours, cooled andthe solvent removed in vacuo. The resulting solid was dissolved in 50 mlmethylene chloride under N₂ and 1.37 g (8.6 mmol)2-amino-4-chloro-6-methylpyrimidine added with 0.01 g (0.1 mmol) ofDABCO. The mixture was stirred overnight and the solvent removed invacuo. The residue was triturated with 1-chlorobutane. The resultingsolid was dissolved in cold 1% NaOH, filtered and precipitated with 10%HCl washed with water and air dried to provide 0.46 g of the titlecompound. m.p. 179°-180° C.

NMR (DMSO-d₆): δ 2.48 (s, 6, SCH₃); 4.00 (s, 3, OCH₃); 6.90 (s, 1, ArH);7.18-7.79 (m, 3, ArH); 10.88 (brs, 1, NH); and 12.48 (brs, 1, NH).

IR (nujol): 5.80 (c=o).

Following the procedures described above, the compounds in Tables 1-5can be prepared. In these tables, some variables are defined twice,there being a different definition when Z=CH and when Z=N. Thus, forexample, in the thirteenth row in Table 3, X is defined as Cl, but, whenZ=N (definition a), then X is defined as OCF₂ H. Similarly, in Table 3and the following tables, when a row is followed by a superscript, thosesubstituent definitions apply only when Z has the definition denoted bythe superscript.

                                      TABLE 1                                     __________________________________________________________________________     ##STR47##                                                                    R.sub.1                                                                            R.sub.2                                                                           R.sub.3                                                                         A  L  X.sub.1                                                                            Y.sub.1                                                                           X.sub.2                                                                            Y.sub.2                                                                           Y.sub.3                                    __________________________________________________________________________    SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-2                                                                              O  CH.sub.3                                                                           --  --   --  --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-2                                                                              O  OCH.sub.3                                                                          --  --   --  --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-2                                                                              CH.sub.2                                                                         CH.sub.3                                                                           --  --   --  --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-2                                                                              CH.sub.2                                                                         OCH.sub.3                                                                          --  --   --  --                                         SCH.sub.3                                                                          SCH.sub.3                                                                         H A-2                                                                              O  CH.sub.3                                                                           --  --   --  --                                         SCH.sub.3                                                                          SCH.sub.3                                                                         H A-2                                                                              O  OCH.sub.3                                                                          --  --   --  --                                         SO.sub.2 CH.sub. 3                                                                 C.sub.6 H.sub.5                                                                   H A-2                                                                              O  Cl   --  --   --  --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-2                                                                              O  OCF.sub.2 H                                                                        --  --   --  --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-3                                                                              -- CH.sub.3                                                                           --  --   --  --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-3                                                                              -- OCH.sub.3                                                                          --  --   --  --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-3                                                                              -- Cl   --  --   --  --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-3                                                                              -- OCF.sub.2 H                                                                        --  --   --  --                                         SCH.sub.3                                                                          SCH.sub.3                                                                         H A-3                                                                              -- OCH.sub.3                                                                          --  --   --  --                                         SCH.sub.3                                                                          SCH.sub.3                                                                         H A-3                                                                              -- CH.sub.3                                                                           --  --   --  --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-4                                                                              -- CH.sub.3                                                                           --  --   --  CH.sub.3                                   SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-4                                                                              -- OCH.sub.3                                                                          --  --   --  CH.sub. 3                                  SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-4                                                                              -- Cl   --  --   --  H                                          SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-4                                                                              -- OCF.sub.2 H                                                                        --  --   --  CH.sub.3                                   SCH.sub.3                                                                          SCH.sub.3                                                                         H A-4                                                                              -- OCH.sub.3                                                                          --  --   --  CH.sub.3                                   SCH.sub.3                                                                          SCH.sub.3                                                                         H A-4                                                                              -- CH.sub.3                                                                           --  --   --  H                                          SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-5                                                                              -- --   CH.sub.3                                                                          --   --  --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-5                                                                              -- --   OCH.sub.3                                                                         --   --  --                                         SCH.sub.3                                                                          SCH.sub.3                                                                         H A-5                                                                              -- --   CH.sub.3                                                                          --   --  --                                         SCH.sub.3                                                                          SCH.sub.3                                                                         H A-5                                                                              -- --   OCH.sub.3                                                                         --   --  --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-6                                                                              -- --   --  CH.sub.3                                                                           CH.sub.3                                                                          --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-6                                                                              -- --   --  CH.sub.3                                                                           OCH.sub. 3                                                                        --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-6                                                                              -- --   --  CH.sub.3                                                                           SCH.sub.3                                                                         --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-6                                                                              -- --   --  CH.sub.2 CH.sub.3                                                                  CH.sub.3                                                                          --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-6                                                                              -- --   --  CH.sub.2 CH.sub.3                                                                  OCH.sub.3                                                                         --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-6                                                                              -- --   --  CH.sub.2 CH.sub.3                                                                  SCH.sub.3                                                                         --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-6                                                                              -- --   --  CH.sub.2 CF.sub.3                                                                  CH.sub.3                                                                          --                                         SO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                   H A-6                                                                              -- --   --  CH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                         --                                         SCH.sub.3                                                                          SCH.sub.3                                                                         H A-6                                                                              -- --   --  CH.sub.3                                                                           CH.sub.3                                                                          --                                         SCH.sub.3                                                                          SCH.sub.3                                                                         H A-6                                                                              -- --   --  CH.sub.3                                                                           OCH.sub.3                                                                         --                                         __________________________________________________________________________

                                      TABLE 2a                                    __________________________________________________________________________     ##STR48##                                                                                                                m.p.                              R.sub.1     R.sub.2     R.sub.3                                                                            X     Y        (°C.)                      __________________________________________________________________________    SCH.sub.3   SCH.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.2 CH.sub.3                                                                        SCH.sub.2 CH.sub.3                                                                        3-Cl CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.2 CH.sub.3                                                                        SCH.sub.2 CH.sub.2 CH.sub.3                                                               H    OCH.sub.3                                                                           OCH.sub.3                                  SCH.sub.2 CH.sub.2 CH.sub.3                                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                               H    CH.sub.3                                                                            OCH.sub.3                                  S(O)CH.sub.3                                                                              SCH.sub.3   H    CH.sub.3                                                                            CH.sub.3                                   S(O).sub.2 CH.sub.3                                                                       SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.3                                  S(O)CH.sub.3                                                                              S(O)CH.sub.3                                                                              H    OCH.sub.3                                                                           OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                       S(O)CH.sub.3                                                                              H    Cl    OCH.sub.3                                  SCH.sub.3   N(CH.sub.3).sub.2                                                                         H    CH.sub.3                                                                            OCH.sub.3                                  S(O)CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         H    OCH.sub.3                                                                           OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                       N(CH.sub.3).sub.2                                                                         H    Cl    OCH.sub.3                                  SCH.sub.3   N(CH.sub.3)CH.sub.2 CH.sub.3                                                              3-F  CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3   N(CH.sub.2 CH.sub.3).sub.2                                                                H    OCH.sub.3                                                                           OCH.sub.3                                  CF.sub.3    CF.sub.3    H    CH.sub.3                                                                            OCH.sub.3                                  CF.sub.3    CF.sub.3    4-Br CH.sub.3                                                                            CH.sub.3                                   N(CH.sub.3).sub.2                                                                         N(CH.sub.3).sub.2                                                                         H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3)CH.sub.2 CH.sub.3                                                              N(CH.sub.3).sub.2                                                                         H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.2 CH.sub.3).sub.2                                                                N(CH.sub.3).sub.2                                                                         4-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3)CH.sub.2 CH.sub.3                                                              N(CH.sub.3)CH.sub.2 CH.sub.3                                                              H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.2 CH.sub.3).sub.2                                                                N(CH.sub.2 CH.sub.3).sub.2                                                                H    Cl    OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         2'-C.sub.6 H.sub.4 Cl                                                                     H    Cl    OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 CO.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                            CH.sub.3                                   N(CH.sub.3).sub.2                                                                         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                       H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub. 2                                                                        CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                              H    Cl    OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 CO.sub.2 CH.sub.2 CHCH.sub.2                                                     H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                    5-OCH.sub.3                                                                        CH.sub.3                                                                            CH.sub.3                                   N(CH.sub.3).sub.2                                                                         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                             H    CH.sub.3                                                                            CH.sub.3                                   N(CH.sub.3).sub.2                                                                          ##STR49##  H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                          ##STR50##  H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         OSO.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         OSO.sub.2 CH.sub.2 CH.sub.3                                                               3-CF.sub.3                                                                         Cl    OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         OSO.sub.2 CF.sub.3                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 OCH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 OCH.sub.2 CH.sub.3                                                               H    CH.sub.3                                                                            CH.sub. 3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3                                                      H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 OCF.sub.2 H                                                                      H    CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         SO.sub.2 N(CH.sub.3).sub.2                                                                H    CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         SO.sub.2 N(CH.sub.3)OCH.sub.3                                                             H    CH.sub.3                                                                            CH.sub.3                                   CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             SO.sub.2 N(CH.sub.3).sub.2                                                                H    OCH.sub.3                                                                           OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         2'-C.sub.6 H.sub.4 OCH.sub.3                                                              H    OCH.sub.3                                                                           OCH.sub.3                                  CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       3'-C.sub.6 H.sub.4 CH.sub.3                                                               H    CH.sub.3                                                                            CH.sub.3                                   CO.sub.2 CH.sub.3                                                                         CH.sub.2 CO.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                              ##STR51##  H    OCH.sub.3                                                                           OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         CH.sub.2 OCH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         CH.sub.2 OCF.sub.2 H                                                                      H    OCH.sub.3                                                                           OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub. 2                                                               SO.sub.2 N(CH.sub.3).sub.2                                                                H    CH.sub.3                                                                            CH.sub.3                                   SO.sub.2 N(CH.sub.3)OCH.sub.3                                                             SO.sub.2 N(CH.sub.3).sub.3                                                                H    CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 N(CH.sub.3)OCH.sub.3                                                             SO.sub.2 N(CH.sub.3)OCH.sub.3                                                             H    CH.sub.3                                                                            CH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                                C.sub.6 H.sub.5                                                                           H    OCH.sub.3                                                                           OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                4'-C.sub.6 H.sub.4 Cl                                                                     H    CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                2'-C.sub.6 H.sub.4 OCH.sub.3                                                              H    OCH.sub.3                                                                           OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                CH.sub.2 CO.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                 ##STR52##  H    CH.sub.3                                                                            CH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                                OSO.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                OSO.sub.2 CF.sub.3                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                  C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                           2'-C.sub.6 H.sub.4 Cl                                                                     H    OCH.sub.3                                                                           OCH.sub.3                                  C.sub.6 H.sub.5                                                                           3'-C.sub. 6 H.sub.4 Cl                                                                    H    CH.sub.3                                                                            OCH.sub.3                                   ##STR53##                                                                                 ##STR54##  H    OCH.sub.3                                                                           OCH.sub.3                                   ##STR55##                                                                                 ##STR56##  H    CH.sub.3                                                                            CH.sub.3                                   C.sub.6 H.sub.5                                                                           CH.sub.2 CO.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                            ##STR57##  H    OCH.sub.3                                                                           OCH.sub.3                                  2'-C.sub.6 H.sub.4 CH.sub.3                                                               CH.sub.2 CO.sub.2 CH.sub.3                                                                H    Cl    OCH.sub.3                                  C.sub.6 H.sub.5                                                                           OSO.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                           OSO.sub.2 CF.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  2'-C.sub.6 H.sub.4 F                                                                      OSO.sub.2 CH.sub.2 CH.sub.3                                                               H    OCH.sub.3                                                                           OCH.sub.3                                  C.sub.6 H.sub.5                                                                           CH.sub.2 OCH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  4'-C.sub.6 H.sub.4 Cl                                                                     CH.sub.2 OCF.sub.2 H                                                                      H    CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                                CH.sub.2 CO.sub.2 CH.sub.3                                                                3-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                                CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                    H    CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                             CH.sub.2 CO.sub.2 CH.sub.2 CHCH.sub.2                                                     H    CH.sub.3                                                                            OCH.sub.3                                   ##STR58##  CH.sub.2 CO.sub.2 CH.sub.3                                                                H    OCH.sub.3                                                                           OCH.sub.3                                   ##STR59##  CH.sub.2 CO.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                            CH.sub.3                                    ##STR60##                                                                                 ##STR61##  H    OCH.sub.3                                                                           CH.sub.3                                   CH.sub.2 CO.sub.2 CH.sub.3                                                                OSO.sub.2 CH.sub.3                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                   ##STR62##  OSO.sub.2 CF.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                                CH.sub.2 OCH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                   ##STR63##  CH.sub.2 OCF.sub.2 H                                                                      H    CH.sub.3                                                                            CH.sub.3                                   OSO.sub.2 CH.sub.3                                                                        OSO.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  OSO.sub.2 CF.sub.3                                                                        OSO.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            CH.sub.3                                   OSO.sub.2 CF.sub.3                                                                        OSO.sub.2 CF.sub.3                                                                        H    CH.sub.3                                                                            CH.sub.3                                   OSO.sub.2 CH.sub.3                                                                        CH.sub.2 OCH.sub.3                                                                        4-CF.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                  OSO.sub.2 CF.sub.3                                                                        CH.sub.2 OCH.sub.3                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                        CH.sub.2 OCF.sub.2 H                                                                      H    CH.sub.3                                                                            OCH.sub.3                                  OSO.sub.2 CF.sub.3                                                                        CH.sub.2 OCF.sub.2 H                                                                      5-Cl CH.sub.3                                                                            CH.sub.3                                   CH.sub.2 OCH.sub.3                                                                        CH.sub.2 OCH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                      CH.sub.2 OCH.sub.3                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                      CH.sub.2 OCF.sub.2 H                                                                      H    CH.sub.3                                                                            CH.sub.3                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            CH.sub.3 228-230° d                 SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.3                                                                              206-208° d                 SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    CH    CF.sub.3                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3                         SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           3-Cl CH.sub.3                                                                            CH.sub.2 OCH.sub.3                         SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            CH.sub.3 188-194° d                 SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.3                                                                              206-208° d                 SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            CF.sub.3                                   SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            H                                          SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            NH.sub.2                                   SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            NHCH.sub.3                                 SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            N(CH.sub.3).sub.2                          SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            CH.sub.2 CH.sub.3                          SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            CH.sub.2 OCH.sub.2 CH.sub.3                SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.2 CH.sub.3                         SCH.sub.3   SCH.sub.3   5-CF.sub.3                                                                         CH.sub.3                                                                            OCH.sub.2 CH.sub.3                         SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            SCH.sub.3                                  SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                       SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.2 C CH                             SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.2 CH.sub.2 F                       SCH.sub.3   C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.2 CH.sub.2 Cl                      SCH.sub. 3  C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.2 CH.sub.2 Br                      SCH.sub.3   SCH.sub.3   3-Cl CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3   SCH.sub.3   3-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                         2'-C.sub.6 H.sub.4 Cl                                                                     H    CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                         3-Cl        CH.sub.3                                                                           OCH.sub.3                                        SO.sub.2 CH.sub.3                                                                         5-Cl        CH.sub.3                                                                           OCH.sub.3                                        SO.sub.2 CH.sub.3                                                                         H           OCH.sub.3                                                                          CF.sub.3                                         SO.sub.2 CH.sub.3                                                                         H           OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                               SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.3                                                                           OCH.sub.3                                                                              212-214° d                 SO.sub.2 CH.sub.3                                                                         H           OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                               SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                           CF.sub.3                                   SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                           OCH.sub.3                                                                              220-225° d                 SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                         SCH.sub.3   SCH.sub.3   3-Cl CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3   SCH.sub.3   3-OCH.sub.3                                                                        OCH.sub.3                                                                           OCH.sub.3                                  SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                           N(CH.sub.3).sub.2                          SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                           CH.sub.2 CH.sub.3                          SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                           SCH.sub.3                                  SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    Cl    NH.sub.2                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    Cl    NHCH.sub.3                                 SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    Cl    N(CH.sub.3).sub.2                          SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    Cl    OCH.sub.3                                  SCH.sub.3   SCH.sub.3   H    Cl    OCH.sub.3                                                                              179-186°                   SCH.sub.3   SCH.sub.3   H    Cl    N(CH.sub.3).sub.2                          SCH.sub.3   SCH.sub.3   3-Cl CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3   SCH.sub.3   3-CH.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.2 CH.sub.3                                                                  H                                          SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.2 CH.sub.3                                                                  CH.sub.3                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.2 CH.sub.3                                                                  CF.sub.3                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.2 CH.sub.3                                                                  CH.sub.2 OCH.sub.3                         SCH.sub.3   SCH.sub.3   H    OCH.sub.2 CH.sub.3                                                                  CH.sub.3                                   SCH.sub.3   SCH.sub.3   H    OCH.sub.2 CH.sub.3                                                                  CF.sub.3                                   SCH.sub.3   SCH.sub.3   3-OCH.sub.3                                                                        OCH.sub.2 CH.sub.3                                                                  CH.sub.3                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    F     OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    F     NH.sub. 2                                  SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    F     NHCH.sub.3                                 SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    F     N(CH.sub.3).sub.2                          SCH.sub.3   SCH.sub.3   H    F     OCH.sub.3                                  SCH.sub.3   SCH.sub.3   H    F     N(CH.sub.3).sub.2                          SCH.sub.3   C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            CH.sub.3 218-221° d                 SCH.sub.3   C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.3                                                                              170-173°                   SCH.sub.3   C.sub.6 H.sub.5                                                                           H    OCH.sub.3                                                                           OCH.sub.3                                                                              187-189°                   __________________________________________________________________________

                                      TABLE 2b                                    __________________________________________________________________________     ##STR64##                                                                    R.sub.1     R.sub.2     R.sub.3                                                                            X     Y        m.p. (°C.)                 __________________________________________________________________________    SCH.sub.3   SCH.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.2 CH.sub.3                                                                        SCH.sub.2 CH.sub.3                                                                        3-Cl CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.2 CH.sub.3                                                                        SCH.sub.2 CH.sub.2 CH.sub.3                                                               H    OCH.sub.3                                                                           OCH.sub.3                                  SCH.sub.2 CH.sub.2 CH.sub.3                                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                               H    CH.sub.3                                                                            OCH.sub.3                                  S(O)CH.sub.3                                                                              SCH.sub.3   H    CH.sub.3                                                                            CH.sub.3                                   S(O).sub.2 CH.sub.3                                                                       SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.3                                  S(O)CH.sub.3                                                                              S(O)CH.sub.3                                                                              H    OCH.sub.3                                                                           OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                       S(O)CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3   N(CH.sub.3).sub.2                                                                         H    CH.sub.3                                                                            OCH.sub.3                                  S(O)CH.sub.3                                                                              N(CH.sub. 3).sub.2                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                       N(CH.sub.3).sub.2                                                                         H    CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3   N(CH.sub.3)CH.sub.2 CH.sub.3                                                              3-F  CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3   N(CH.sub.2 CH.sub.3).sub.2                                                                H    OCH.sub.3                                                                           OCH.sub.3                                  CF.sub.3    CF.sub.3    H    CH.sub.3                                                                            OCH.sub.3                                  CF.sub.3    CF.sub.3    4-Br CH.sub.3                                                                            CH.sub.3                                   N(CH.sub.3).sub.2                                                                         N(CH.sub.3).sub.2                                                                         H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3)CH.sub.2 CH.sub.3                                                              N(CH.sub.3).sub.2                                                                         H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.2 CH.sub.3).sub.2                                                                N(CH.sub.3).sub.2                                                                         4-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3)CH.sub.2 CH.sub.3                                                              N(CH.sub.3)CH.sub.2 CH.sub.3                                                              H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.2 CH.sub.3).sub.2                                                                N(CH.sub.2 CH.sub.3).sub.2                                                                H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         2'-C.sub.6 H.sub.4 Cl                                                                     H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 CO.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                            CH.sub.3                                   N(CH.sub.3).sub.2                                                                         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                       H    CH.sub. 3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                              H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 CO.sub.2 CH.sub.2 CHCH.sub.2                                                     H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                    5-OCH.sub.3                                                                        CH.sub.3                                                                            CH.sub.3                                   N(CH.sub.3).sub.2                                                                         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                             H    CH.sub.3                                                                            CH.sub.3                                   N(CH.sub.3).sub.2                                                                          ##STR65##  H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                          ##STR66##  H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         OSO.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         OSO.sub.2 CH.sub.2 CH.sub.3                                                               3-CF.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         OSO.sub.2 CF.sub.3                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 OCH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 OCH.sub.2 CH.sub.3                                                               H    CH.sub.3                                                                            CH.sub.3                                   N(CH.sub.3).sub.2                                                                         CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3                                                      H    OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                         CH.sub.2 OCF.sub.2 H                                                                      H    CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         SO.sub.2 N(CH.sub.3).sub.2                                                                H    CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         SO.sub.2 N(CH.sub.3)OCH.sub.3                                                             H    CH.sub.3                                                                            CH.sub.3                                   CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             SO.sub.2 N(CH.sub.3).sub.2                                                                H    OCH.sub.3                                                                           OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         2'-C.sub.6 H.sub.4 OCH.sub.3                                                              H    OCH.sub.3                                                                           OCH.sub.3                                  CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       3'-C.sub.6 H.sub.4 CH.sub.3                                                               H    CH.sub.3                                                                            CH.sub.3                                   CO.sub.2 CH.sub.3                                                                         CH.sub.2 CO.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                              ##STR67##  H    OCH.sub.3                                                                           OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         CH.sub.2 OCH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                         CH.sub.2 OCF.sub.2 H                                                                      H    OCH.sub.3                                                                           OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                SO.sub.2 N(CH.sub.3).sub.2                                                                H    CH.sub.3                                                                            CH.sub.3                                   SO.sub.2 N(CH.sub.3)OCH.sub.3                                                             SO.sub.2 N(CH.sub.3).sub.3                                                                H    CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 N(CH.sub.3)OCH.sub.3                                                             SO.sub.2 N(CH.sub.3)OCH.sub.3                                                             H    CH.sub.3                                                                            CH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                                C.sub.6 H.sub.5                                                                           H    OCH.sub.3                                                                           OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                4'-C.sub.6 H.sub.4 Cl                                                                     H    CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                2'-C.sub.6 H.sub.4 OCH.sub.3                                                              H    OCH.sub.3                                                                           OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                CH.sub.2 CO.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                 ##STR68##  H    CH.sub.3                                                                            CH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                                OSO.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                OSO.sub.2 CF.sub.3                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                  C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                           2'-C.sub.6 H.sub.4 Cl                                                                     H    OCH.sub.3                                                                           OCH.sub. 3                                 C.sub.6 H.sub.5                                                                           3'-C.sub.6 H.sub.4 Cl                                                                     H    CH.sub.3                                                                            OCH.sub.3                                   ##STR69##                                                                                 ##STR70##  H    OCH.sub.3                                                                           OCH.sub.3                                   ##STR71##                                                                                 ##STR72##  H    CH.sub.3                                                                            CH.sub.3                                   C.sub.6 H.sub.5                                                                           CH.sub.2 CO.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                            ##STR73##  H    OCH.sub.3                                                                           OCH.sub.3                                  2'-C.sub.6 H.sub.4 CH.sub.3                                                               CH.sub.2 CO.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                           OSO.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                           OSO.sub.2 CF.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  2'-C.sub.6 H.sub.4 F                                                                      OSO.sub.2 CH.sub.2 CH.sub.3                                                               H    OCH.sub.3                                                                           OCH.sub.3                                  C.sub.6 H.sub.5                                                                           CH.sub.2 OCH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  4'-C.sub.6 H.sub.4 Cl                                                                     CH.sub.2 OCF.sub.2 H                                                                      H    CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                                CH.sub.2 CO.sub.2 CH.sub.3                                                                3-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                                CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                    H    CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                             CH.sub.2 CO.sub.2 CH.sub.2 CHCH.sub.2                                                     H    CH.sub.3                                                                            OCH.sub.3                                   ##STR74##  CH.sub.2 CO.sub.2 CH.sub.3                                                                H    OCH.sub.3                                                                           OCH.sub.3                                   ##STR75##  CH.sub.2 CO.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                            CH.sub.3                                    ##STR76##                                                                                 ##STR77##  H    OCH.sub.3                                                                           CH.sub.3                                   CH.sub.2 CO.sub.2 CH.sub.3                                                                OSO.sub.2 CH.sub.3                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                   ##STR78##  OSO.sub.2 CF.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                                CH.sub.2 OCH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                   ##STR79##  CH.sub.2 OCF.sub.2 H                                                                      H    CH.sub.3                                                                            CH.sub.3                                   OSO.sub.2 CH.sub.3                                                                        OSO.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  OSO.sub.2 CF.sub.3                                                                        OSO.sub.2 CH.sub.3                                                                        H    CH.sub.3                                                                            CH.sub.3                                   OSO.sub.2 CF.sub.3                                                                        OSO.sub.2 CF.sub.3                                                                        H    CH.sub.3                                                                            CH.sub.3                                   OSO.sub.2 CH.sub.3                                                                        CH.sub.2 OCH.sub.3                                                                        4-CF.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                  OSO.sub.2 CF.sub.3                                                                        CH.sub.2 OCH.sub.3                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                        CH.sub.2 OCF.sub.2 H                                                                      H    CH.sub.3                                                                            OCH.sub.3                                  OSO.sub.2 CF.sub.3                                                                        CH.sub.2 OCF.sub.2 H                                                                      5-Cl CH.sub.3                                                                            CH.sub.3                                   CH.sub.2 OCH.sub.3                                                                        CH.sub.2 OCH.sub.3                                                                        H    CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                      CH.sub.2 OCH.sub.3                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                      CH.sub.2 OCF.sub.2 H                                                                      H    CH.sub.3                                                                            CH.sub.3                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            CH.sub.3                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.3                                                                              204-208° d.                SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    CH    CF.sub.3                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3                         SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           3-Cl CH.sub.3                                                                            CH.sub.2 OCH.sub.3                         SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.2 CF.sub.3                         SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            CH.sub.3 179-193°                   SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            CF.sub.3                                   SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            H                                          SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            NH.sub.2                                   SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            NHCH.sub.3                                 SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            N(CH.sub.3).sub.2                          SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            CH.sub.2 CH.sub.3                          SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            CH.sub.2 OCH.sub.2 CH.sub.3                SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.2 CH.sub.3                         SCH.sub.3   SCH.sub.3   5-CF.sub.3                                                                         CH.sub.3                                                                            OCH.sub.2 CH.sub.3                         SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            SCH.sub.3                                  SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                       SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.2 CCH                              SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                            OCH.sub.2 CH.sub.2 F                       SCH.sub. 3  C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.2 CH.sub.2 Cl                      SCH.sub.3   C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                            OCH.sub.2 CH.sub.2 Br                      SCH.sub.3   SCH.sub.3   3-Cl CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3   SCH.sub.3   3-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                         2'-C.sub.6 H.sub.4 Cl                                                                     H    CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           3-Cl CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           5-Cl CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.3                                                                           CF.sub.3                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                         SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.3                                                                           OCH.sub.3                                                                              216-220° d.                SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.3                                                                           OCH.sub.2 CF.sub.3                         SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                           CF.sub.3                                   SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                           OCH.sub.3                                                                              121-132°                   SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                         SCH.sub.3   SCH.sub.3   3-Cl CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3   SCH.sub.3   3-OCH.sub.3                                                                        OCH.sub.3                                                                           OCH.sub.3                                  SCH.sub.3   SCH.sub. 3  H    OCH.sub.3                                                                           N(CH.sub.3).sub.2                          SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                           CH.sub.2 CH.sub.3                          SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                           SCH.sub.3                                  SCH.sub.3   SCH.sub.3   3-Cl CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3   SCH.sub.3   3-CH.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.2 CH.sub.3                                                                  H                                          SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.2 CH.sub.3                                                                  CH.sub.3                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.2 CH.sub.3                                                                  CF.sub.3                                   SO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                           H    OCH.sub.2 CH.sub.3                                                                  CH.sub.2 OCH.sub.3                         SCH.sub.3   SCH.sub.3   H    OCH.sub.2 CH.sub.3                                                                  CH.sub.3                                   SCH.sub.3   SCH.sub.3   H    OCH.sub.2 CH.sub.3                                                                  CF.sub.3                                   SCH.sub.3   SCH.sub.3   3-OCH.sub.3                                                                        OCH.sub.2 CH.sub.3                                                                  CH.sub.3                                   SCH.sub.3   C.sub.6 H.sub.5                                                                           H    OCH.sub.3                                                                           CH.sub.3 130-135° d.                __________________________________________________________________________

                  TABLE 3                                                         ______________________________________                                         ##STR80##                                                                    (Z = a.) (N or b.) CH                                                         R.sub.1    R.sub.2     R.sub.3  X      Y                                      ______________________________________                                        SCH.sub.3  SCH.sub.2 CH.sub.3                                                                        H        CH.sub.3                                                                             CH.sub.3                               SCH.sub.3  SCH.sub.2 CH.sub.3                                                                        H        CH.sub.3                                                                             OCH.sub.3                              SCH.sub.3  SCH.sub.2 CH.sub.3                                                                        5-CF.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                              SCH.sub.3  SCH.sub.2 CH.sub.3                                                                        H        OCH.sub.3                                                                            OCH.sub.3                              SCH.sub.3  SCH.sub.2 CH.sub.3                                                                        3-Cl     OCH.sub.3                                                                            OCH.sub.3                              SCH.sub.3  SCH.sub.2 CH.sub.2 CH.sub.3                                                               H        CH.sub.3                                                                             OCH.sub.3                              SCH.sub.3  SCH.sub.2 CH.sub.2 CH.sub.3                                                               H        OCH.sub.3                                                                            OCH.sub.3                              SCH.sub.2 CH.sub.2 CH.sub.3                                                              SCH.sub.2 CH.sub.2 CH.sub.3                                                               H        CH.sub.3                                                                             OCH.sub.3                              SCH.sub.2 CH.sub.2 CH.sub. 3                                                             SCH.sub.2 CH.sub.2 CH.sub.3                                                               H        OCH.sub.3                                                                            OCH.sub.3                              SCH.sub.2 CH.sub.2 CH.sub.3                                                              SCH.sub.2 CH.sub.2 CH.sub.3                                                               4-OCH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                              S(O)CH.sub.3                                                                             SCH.sub.3   H        CH.sub.3                                                                             OCH.sub.3                              S(O)CH.sub.3                                                                             S(O)CH.sub.3                                                                              H        OCH.sub.3                                                                            OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                      S(O)CH.sub.3                                                                              H        Cl.sup.b                                                                             OCH.sub.3                              N(CH.sub.3).sub.2                                                                        C.sub.6 H.sub.5                                                                           H        CH.sub.3                                                                             CH.sub.3                               N(CH.sub.3).sub.2                                                                        C.sub.6 H.sub.5                                                                           H        CH.sub.3                                                                             OCH.sub.3                              N(CH.sub.3).sub.2                                                                        C.sub.6 H.sub.5                                                                           H        OCH.sub.3                                                                            OCH.sub.3                              N(CH.sub.3).sub.2                                                                        C.sub.6 H.sub.5                                                                           H        Cl.sup.b                                                                             OCH.sub.3                              N(CH.sub.3).sub.2                                                                        N(CH.sub.3).sub.2                                                                         H        CH.sub.3                                                                             OCH.sub.3                              N(CH.sub.3).sub.2                                                                        N(CH.sub.3).sub.2                                                                         H        OCH.sub.3                                                                            OCH.sub.3                              N(CH.sub.3).sub.2                                                                        N(CH.sub.3).sub.2                                                                         H        Cl.sup.b                                                                             OCH.sub.3                              CF.sub.3   CF.sub.3    H        CH.sub.3                                                                             CH.sub.3                               CF.sub.3   CF.sub.3    H        CH.sub.3                                                                             OCH.sub.3                              CF.sub.3   CF.sub.3    H        OCH.sub.3                                                                            OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        C.sub.6 H.sub.5                                                                           H        CH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        C.sub.6 H.sub.5                                                                           H        OCH.sub.3                                                                            OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        C.sub.6 H.sub.5                                                                           H        Cl.sup.b                                                                             OCH.sub.3                              OSO.sub.2 N(CH.sub.3).sub.2                                                              C.sub.6 H.sub.5                                                                           H        CH.sub.3                                                                             OCH.sub.3                              OSO.sub.2 N(CH.sub.3).sub.2                                                              C.sub.6 H.sub.5                                                                           H        OCH.sub.3                                                                            OCH.sub.3                              C.sub.6 H.sub.5                                                                          C.sub.6 H.sub.5                                                                           H        CH.sub.3                                                                             CH.sub.3                               C.sub.6 H.sub.5                                                                          C.sub.6 H.sub.5                                                                           H        CH.sub.3                                                                             OCH.sub.3                              C.sub.6 H.sub.5                                                                          C.sub.6 H.sub.5                                                                           H        OCH.sub.3                                                                            OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                       C.sub.6 H.sub.5                                                                           H        CH.sub.3                                                                             OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                       C.sub.6 H.sub.5                                                                           H        OCH.sub.3                                                                            OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                       OSO.sub.2 CH.sub.3                                                                        H        CH.sub.3                                                                             CH.sub.3                               OSO.sub.2 CH.sub.3                                                                       OSO.sub.2 CH.sub.3                                                                        H        CH.sub.3                                                                             OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                       OSO.sub.2 CH.sub.3                                                                        H        OCH.sub.3                                                                            OCH.sub.3                              SCH.sub.3  N(CH.sub.3).sub.2                                                                         H        CH.sub.3                                                                             CH.sub.3                               SCH.sub.3  N(CH.sub.3).sub.2                                                                         H        CH.sub.3                                                                             OCH.sub.3                              SCH.sub.3  N(CH.sub.3).sub.2                                                                         H        OCH.sub.3                                                                            OCH.sub.3                              S(O)CH.sub.3                                                                             N(CH.sub.3).sub.2                                                                         H        OCH.sub.3                                                                            OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                      N(CH.sub.3).sub.2                                                                         H        OCH.sub.3                                                                            OCH.sub.3                              ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                         ##STR81##                                                                    Z = .sup.a N or .sup.b CH                                                     R.sub.1    R.sub.3                                                                             R.sub.15                                                                             R.sub.16                                                                           R.sub.17                                                                           X      Y                                    ______________________________________                                        SCH.sub.3  H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H     H      H    H    OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H     CH.sub.3                                                                             H    H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H     H      H    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H     CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                             SCH.sub.2 CH.sub.3                                                                       H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.2 CH.sub.2 CH.sub. 3                                                             H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                             H     H      H    H    CH.sub.3                                                                             CH.sub.3                             S(O)CH.sub.3                                                                             H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                             H     CH.sub.3                                                                             H    H    Cl     OCH.sub.3.sup.b                      S(O)CH.sub.3                                                                             H     H      H    CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                      H     H      H    H    OCH.sub.3                                                                            OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                      H     CH.sub.3                                                                             H    H    CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                      H     H      H    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H     H      H    H    CH.sub.3                                                                             CH.sub.3                             CF.sub.3   H     CH.sub.3                                                                             H    H    OCH.sub.3                                                                            CH.sub.3                             CF.sub.3   H     H      CH.sub.3                                                                           H    OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H     CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                        H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                        H     H      H    H    OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3).sub.2                                                                        H     CH.sub.3                                                                             H    H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                        H     H      CH.sub.3                                                                           H    OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.2 CH.sub.3).sub.2                                                               H     H      H    H    OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                        H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            CO.sub.2 CH.sub.3                                                                        H     CH.sub.3                                                                             H    H    OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                        H     H      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                             CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                               H     H      H    H    OCH.sub.3                                                                            OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                               H     CH.sub.3                                                                             H    CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                          H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                          H     H      H    H    OCH.sub.3                                                                            OCH.sub.3                            C.sub.6 H.sub.5                                                                          H     CH.sub.3                                                                             H    CH.sub.3                                                                           Cl     OCH.sub.3.sup.b                      C.sub.6 H.sub.5                                                                          H     H      CH.sub.3                                                                           H    CH.sub.3                                                                             OCH.sub.3                            2'-C.sub.6 H.sub.4 Cl                                                                    H     H      H    H    OCH.sub.3                                                                            OCH.sub.3                            2'-C.sub.6 H.sub.4 CH.sub.3                                                              H     H      H    H    OCF.sub.2 H                                                                          OCH.sub.3                            2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            3'-C.sub.6 H.sub.4 F                                                                     H     CH.sub. 3                                                                            H    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                            4'-C.sub.6 H.sub.4 Br                                                                    H     CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           Cl     OCH.sub.3.sup.b                      CH.sub.2 CO.sub.2 CH.sub.3                                                               H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                               H     CH.sub.3                                                                             H    H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                               H     H      CH.sub.3                                                                           H    Cl     OCH.sub.3.sup.b                       ##STR82## H     H      H    H    OCH.sub.3                                                                            OCF.sub.2 H                          OCO.sub.2 CH.sub.3                                                                       H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                       H     CH.sub.3                                                                             H    H    OCH.sub.3                                                                            OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                       H     H      CH.sub.3                                                                           CH.sub.3                                                                           Cl     OCH.sub.3.sup.b                      OSO.sub.2 CH.sub.3                                                                       H     CH.sub.3                                                                             CH.sub.3                                                                           H    OCH.sub.3                                                                            OCF.sub.2 H                          OSO.sub.2 CF.sub.3                                                                       H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                       H     H      H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                       H     CH.sub.3                                                                             H    H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                       H     H      CH.sub.3                                                                           H    OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCH.sub.3                                                                       H     CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                             CH.sub.2 OCF.sub.2 H                                                                     H     H      H    H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCF.sub.2 H                                                                     H     CH.sub.3                                                                             H    CH.sub.3                                                                           OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCF.sub.2 H                                                                     H     H      CH.sub.3                                                                           H    Cl     OCH.sub.3.sup.b                      CH.sub.2 OCF.sub.2 H                                                                     H     CH.sub.3                                                                             CH.sub.3                                                                           H    CH.sub.3                                                                             OCH.sub.3                            ______________________________________                                    

                                      TABLE 5                                     __________________________________________________________________________     ##STR83##                                                                     ##STR84##                                                                     ##STR85##                                                                    R.sub.1  R.sub.3                                                                            W   R.sub.15                                                                          R.sub.16                                                                          X    Y                                              __________________________________________________________________________    SCH.sub.3                                                                              H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.3                                                                              H    O   H   H   OCH.sub.3                                                                          OCH.sub.3                                      SCH.sub.3                                                                              H    O   CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.3                                                                              H    O   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      SCH.sub.3                                                                              H    O   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       SCH.sub.3                                                                              3-CH.sub.3                                                                         O   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.2 CH.sub.3                                                                     H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      SCH.sub. 2 CH.sub.2 CH.sub.3                                                           H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      S(O)CH.sub.3                                                                           H    O   H   H   CH.sub.3                                                                           CH.sub.3                                       S(O)CH.sub.3                                                                           H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      S(O)CH.sub.3                                                                           H    O   CH.sub.3                                                                          H   Cl.sup.b,d,f                                                                       OCH.sub.3                                      S(O)CH.sub.3                                                                           H    O   H   CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      S(O).sub.2 CH.sub.3                                                                    H    O   H   H   OCH.sub.3                                                                          OCH.sub.3                                      S(O).sub.2 CH.sub.3                                                                    H    O   CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      S(O).sub.2 CH.sub.3                                                                    H    O   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      CF.sub.3 H    O   H   H   CH.sub.3                                                                           CH.sub.3                                       CF.sub.3 H    O   CH.sub.3                                                                          H   OCH.sub.3                                                                          CH.sub.3                                       CF.sub.3 H    O   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      CF.sub.3 H    O   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    O   H   H   OCH.sub.3                                                                          OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    O   CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    O   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      N(CH.sub.3)CH.sub.2 CH.sub.3                                                           H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub. 2 CH.sub.3).sub.2                                                            H    O   H   H   OCH.sub.3                                                                          OCH.sub.3                                      CO.sub.2 CH.sub.3                                                                      H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      CO.sub.2 CH.sub.3                                                                      H    O   CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      CO.sub.2 CH.sub.3                                                                      H    O   H   CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                          H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      SO.sub.2 N(CH.sub.3).sub.2                                                             H    O   H   H   OCH.sub.3                                                                          OCH.sub.3                                      SO.sub.2 N(CH.sub.3).sub.2                                                             H    O   CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    O   H   H   CH.sub.3                                                                           CH.sub.3                                       C.sub.6 H.sub.5                                                                        H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    O   H   H   OCH.sub.3                                                                          OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    O   CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    O   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    O   CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                          OCF.sub.2 H                                    2'-C.sub.6 H.sub.4 Cl                                                                  H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      2'-C.sub.6 H.sub.4 OCH.sub.3                                                           H    O   H   H   OCH.sub.3                                                                          OCH.sub. 3                                     2'-C.sub.6 H.sub.4 CH.sub.3                                                            H    O   H   H   Cl.sup.b,d,f                                                                       OCH.sub.3                                      3'-C.sub.6 H.sub.4 Br                                                                  H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      4'-C.sub.6 H.sub.4 F                                                                   H    O   H   H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub.2 CO.sub.2 CH.sub.3                                                             H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      CH.sub.2 CO.sub.2 CH.sub.3                                                             H    O   CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub.2 CO.sub.2 CH.sub.3                                                             H    O   H   CH.sub.3                                                                          Cl.sup.b,d,f                                                                       OCH.sub.3                                       ##STR86##                                                                             H    O   H   H   OCH.sub.3                                                                          OCF.sub.2 H                                    OSO.sub.2 CH.sub.3                                                                     H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      OSO.sub.2 CH.sub.3                                                                     H    O   CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      OSO.sub.2 CH.sub.3                                                                     H    O   H   CH.sub.3                                                                          Cl.sup.b,d,f                                                                       OCH.sub.3                                      OSO.sub.2 CH.sub.3                                                                     H    O   CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                          OCF.sub.2 H                                    OSO.sub.2 CF.sub.3                                                                     H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                     H    O   H   H   CH.sub.3                                                                           OCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                     H    O   CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub. 2 OCH.sub.3                                                                    H    O   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCF.sub.2 H                                    CH.sub.2 OCH.sub.3                                                                     H    O   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       CH.sub.2 OCF.sub.2 H                                                                   H    O   H   H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub.2 OCF.sub.2 H                                                                   H    O   CH.sub.3                                                                          H   OCH.sub.3                                                                          OCF.sub.2 H                                    CH.sub.2 OCF.sub.2 H                                                                   H    O   H   CH.sub.3                                                                          Cl.sup.b,d,f                                                                       OCH.sub.3                                      CH.sub.2 OCF.sub.2 H                                                                   H    O   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.3                                                                              H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.3                                                                              H    NCH.sub.3                                                                         H   H   OCH.sub.3                                                                          OCH.sub.3                                      SCH.sub.3                                                                              H    NCH.sub.3                                                                         CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.3                                                                              H    NCH.sub.3                                                                         H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      SCH.sub.3                                                                              H    NH  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       SCH.sub.3                                                                              3-OCH.sub.3                                                                        NCH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.2 CH.sub.3                                                                     H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.2 CH.sub.2 CH.sub.3                                                            H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      S(O)CH.sub.3                                                                           H    NH  H   H   CH.sub.3                                                                           CH.sub.3                                       S(O)CH.sub.3                                                                           H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      S(O)CH.sub.3                                                                           H    NCH.sub.3                                                                         CH.sub.3                                                                          H   Cl.sup.b,d,f                                                                       OCH.sub.3                                      S(O)CH.sub.3                                                                           H    NCH.sub.3                                                                         H   CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      S(O).sub.2 CH.sub.3                                                                    H    NCH.sub.3                                                                         H   H   OCH.sub.3                                                                          OCH.sub.3                                      S(O).sub.2 CH.sub.3                                                                    H    NCH.sub.3                                                                         CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      S(O).sub.2 CH.sub.3                                                                    H    NCH.sub.3                                                                         H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      CF.sub.3 H    NH  H   H   CH.sub.3                                                                           CH.sub.3                                       CF.sub.3 H    NCH.sub.3                                                                         CH.sub.3                                                                          H   OCH.sub.3                                                                          CH.sub.3                                       CF.sub.3 H    NCH.sub.3                                                                         H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      CF.sub.3 H    NH  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    NCH.sub.3                                                                         H   H   OCH.sub.3                                                                          OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    NCH.sub.3                                                                         CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    NCH.sub.3                                                                         H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      N(CH.sub.3)CH.sub.2 CH.sub.3                                                           H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub.2 CH.sub.3).sub.2                                                             H    NCH.sub.3                                                                         H   H   OCH.sub.3                                                                          OCH.sub.3                                      CO.sub.2 CH.sub.3                                                                      H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      CO.sub.2 CH.sub.3                                                                      H    NCH.sub.3                                                                         CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      CO.sub.2 CH.sub.3                                                                      H    NCH.sub.3                                                                         H   CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                          H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      SO.sub.2 N(CH.sub.3).sub.2                                                             H    NCH.sub.3                                                                         H   H   OCH.sub.3                                                                          OCH.sub.3                                      SO.sub.2 N(CH.sub.3).sub.2                                                             H    NH  CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           CH.sub.3                                       C.sub.6 H.sub.5                                                                        H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    NCH.sub.3                                                                         H   H   OCH.sub.3                                                                          OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    NCH.sub.3                                                                         CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    NCH.sub.3                                                                         H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    NCH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                          OCF.sub.2 H                                    2'-C.sub.6 H.sub.4 Cl                                                                  H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      2'-C.sub.6 H.sub.4 OCH.sub.3                                                           H    NCH.sub.3                                                                         H   H   OCH.sub.3                                                                          OCH.sub. 3                                     2'-C.sub.6 H.sub.4 CH.sub.3                                                            H    NCH.sub.3                                                                         H   H   Cl.sup.b,d,f                                                                       OCH.sub.3                                      3'-C.sub.6 H.sub.4 Br                                                                  H    NH  H   H   CH.sub.3                                                                           OCH.sub.3                                      4'-C.sub.6 H.sub.4 F                                                                   H    NCH.sub.3                                                                         H   H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub.2 CO.sub.2 CH.sub.3                                                             H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      CH.sub.2 CO.sub.2 CH.sub.3                                                             H    NCH.sub.3                                                                         CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub.2 CO.sub.2 CH.sub.3                                                             H    NCH.sub.3                                                                         H   CH.sub.3                                                                          Cl.sup.b,d,f                                                                       OCH.sub.3                                       ##STR87##                                                                             H    NCH.sub.3                                                                         H   H   OCH.sub.3                                                                          OCF.sub.2 H                                    OSO.sub.2 CH.sub.3                                                                     H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      OSO.sub.2 CH.sub.3                                                                     H    NCH.sub.3                                                                         CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      OSO.sub.2 CH.sub.3                                                                     H    NCH.sub.3                                                                         H   CH.sub.3                                                                          Cl.sup.b,d,f                                                                       OCH.sub.3                                      OSO.sub.2 CH.sub.3                                                                     H    NCH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                          OCF.sub.2 H                                    OSO.sub.2 CF.sub.3                                                                     H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                     H    NCH.sub.3                                                                         H   H   CH.sub.3                                                                           OCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                     H    NCH.sub.3                                                                         CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                     H    NH  H   CH.sub.3                                                                          OCH.sub.3                                                                          OCF.sub.2 H                                    CH.sub.2 OCH.sub.3                                                                     H    NCH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       CH.sub.2 OCF.sub.2 H                                                                   H    NCH.sub.3                                                                         H   H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub.2 OCF.sub.2 H                                                                   H    NCH.sub.3                                                                         CH.sub.3                                                                          H   OCH.sub.3                                                                          OCF.sub.2 H                                    CH.sub.2 OCF.sub.2 H                                                                   H    NCH.sub.3                                                                         H   CH.sub.3                                                                          OCF.sub.2 H                                                                        OCH.sub.3                                      CH.sub.2 OCF.sub.2 H                                                                   H    NCH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.3                                                                              H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.3                                                                              H    S   H   H   OCH.sub.3                                                                          OCH.sub.3                                      SCH.sub.3                                                                              H    S   CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.3                                                                              H    S   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      SCH.sub.3                                                                              H    S   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       SCH.sub.3                                                                              3-Cl S   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.2 CH.sub.3                                                                     H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      SCH.sub.2 CH.sub.2 CH.sub.3                                                            H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      S(O)CH.sub.3                                                                           H    S   H   H   CH.sub.3                                                                           CH.sub.3                                       S(O)CH.sub.3                                                                           H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      S(O)CH.sub.3                                                                           H    S   CH.sub.3                                                                          H   Cl.sup.b,d,f                                                                       OCH.sub.3                                      S(O)CH.sub.3                                                                           H    S   H   CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      S(O).sub.2 CH.sub.3                                                                    H    S   H   H   OCH.sub.3                                                                          OCH.sub.3                                      S(O).sub.2 CH.sub.3                                                                    H    S   CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      S(O).sub.2 CH.sub.3                                                                    H    S   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      CF.sub.3 H    S   H   H   CH.sub.3                                                                           CH.sub.3                                       CF.sub.3 H    S   CH.sub.3                                                                          H   OCH.sub.3                                                                          CH.sub.3                                       CF.sub.3 H    O   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      CF.sub.3 H    S   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    S   H   H   OCH.sub.3                                                                          OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    S   CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub.3).sub.2                                                                      H    S   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      N(CH.sub.3)CH.sub.2 CH.sub.3                                                           H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      N(CH.sub.2 CH.sub.3).sub.2                                                             H    S   H   H   OCH.sub.3                                                                          OCH.sub.3                                      CO.sub.2 CH.sub. 3                                                                     H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      CO.sub.2 CH.sub.3                                                                      H    S   CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      CO.sub.2 CH.sub.3                                                                      H    S   H   CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                          H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      SO.sub.2 N(CH.sub.3).sub.2                                                             H    S   H   H   OCH.sub.3                                                                          OCH.sub.3                                      SO.sub.2 N(CH.sub.3).sub.2                                                             H    S   CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    S   H   H   CH.sub.3                                                                           CH.sub.3                                       C.sub.6 H.sub.5                                                                        H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    S   H   H   OCH.sub.3                                                                          OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    S   CH.sub.3                                                                          H   CH.sub.3                                                                           OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    S   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                      C.sub.6 H.sub.5                                                                        H    S   CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                          OCF.sub.2 H                                    2'-C.sub.6 H.sub.4 Cl                                                                  H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      2'-C.sub.6 H.sub.4 OCH.sub.3                                                           H    S   H   H   OCH.sub.3                                                                          OCH.sub.3                                      2'-C.sub.6 H.sub.4 CH.sub.3                                                            H    S   H   H   Cl.sup.b,d,f                                                                       OCH.sub.3                                      3'-C.sub.6 H.sub.4 Br                                                                  H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      4'-C.sub.6 H.sub.4 F                                                                   H    S   H   H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub.2 CO.sub.2 CH.sub.3                                                             H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      CH.sub.2 CO.sub.2 CH.sub.3                                                             H    S   CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub.2 CO.sub.2 CH.sub.3                                                             H    S   H   CH.sub.3                                                                          OCF.sub.2 H                                                                        OCH.sub.3                                       ##STR88##                                                                             H    S   H   H   OCH.sub.3                                                                          OCF.sub.2 H                                    OSO.sub.2 CH.sub.3                                                                     H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      OSO.sub.2 CH.sub.3                                                                     H    S   CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      OSO.sub.2 CH.sub.3                                                                     H    S   H   CH.sub.3                                                                          Cl.sup.b,d,f                                                                       OCH.sub.3                                      OSO.sub.2 CH.sub.3                                                                     H    S   CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                          OCF.sub.2 H                                    OSO.sub.2 CF.sub.3                                                                     H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                     H    S   H   H   CH.sub.3                                                                           OCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                     H    S   CH.sub.3                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                     H    S   H   CH.sub.3                                                                          OCH.sub.3                                                                          OCF.sub.2 H                                    CH.sub.2 OCH.sub. 3                                                                    H    S   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       CH.sub.2 OCF.sub.2 H                                                                   H    S   H   H   OCH.sub.3                                                                          OCH.sub.3                                      CH.sub.2 OCF.sub.2 H                                                                   H    S   CH.sub.3                                                                          H   OCH.sub.3                                                                          OCF.sub.2 H                                    CH.sub.2 OCF.sub.2 H                                                                   H    S   H   CH.sub.3                                                                          Cl.sup.b,d,f                                                                       OCH.sub.3                                      CH.sub.2 OCF.sub.2 H                                                                   H    S   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      __________________________________________________________________________

                  TABLE 6                                                         ______________________________________                                         ##STR89##                                                                     ##STR90##                                                                     ##STR91##                                                                    R.sub.1    R.sub.3                                                                              W'     R.sub.15                                                                            X       Y                                      ______________________________________                                        SCH.sub.3  H      O      H     CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3  H      O      H     OCH.sub.3                                                                             OCH.sub.3                              SCH.sub.3  H      O      CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3  H      O      CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               SCH.sub.2 CH.sub.3                                                                       H      O      H     CH.sub.3                                                                              OCH.sub.3                              SCH.sub.2 CH.sub.2 CH.sub.3                                                              H      O      H     CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                             H      O      H     CH.sub.3                                                                              CH.sub.3                               S(O)CH.sub.3                                                                             H      O      H     CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                             H      O      CH.sub.3                                                                            Cl      OCH.sub.3.sup.b,d,f                    S(O).sub.2 CH.sub.3                                                                      H      O      H     OCH.sub.3                                                                             OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                      H      O      H     CH.sub.3                                                                              OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                      H      O      CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3   H      O      H     CH.sub.3                                                                              CH.sub.3                               CF.sub.3   H      O      H     OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3   H      O      CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                        H      O      H     CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                        H      O      H     OCH.sub.3                                                                             OCH.sub.3                              N(CH.sub.3).sub.2                                                                        H      O      CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H      O      H     CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.2 CH.sub.3).sub.2                                                               H      O      H     OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        H      O      H     CH.sub.3                                                                              OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        H      O      H     OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        H      O      CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H      O      H     CH.sub.3                                                                              OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                               H      O      H     OCH.sub.3                                                                             OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub. 2                                                              H      O      CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                          H      O      H     CH.sub.3                                                                              CH.sub.3                               C.sub.6 H.sub.5                                                                          H      O      H     CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                          H      O      H     OCH.sub.3                                                                             OCH.sub.3                              C.sub.6 H.sub.5                                                                          H      O      CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 Cl                                                                    H      O      H     CH.sub.3                                                                              OCH.sub.3                              2'-C.sub.6 H.sub.4 CH.sub.3                                                              H      O      H     OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H      O      H     OCF.sub.2 H                                                                           OCH.sub.3                              3'-C.sub.6 H.sub.4 Br                                                                    H      O      H     CH.sub.3                                                                              OCH.sub.3                              4'-C.sub.6 H.sub.4 F                                                                     H      O      H     Cl      OCH.sub.3.sup.b,d,f                    CH.sub.2 CO.sub.2 CH.sub.3                                                               H      O      H     CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                               H      O      H     OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                               H      O      CH.sub.3                                                                            Cl      OCH.sub.3.sup.b,d,f                     ##STR92## H      O      H     OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CH.sub.3                                                                       H      O      H     CH.sub.3                                                                              OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                       H      O      H     OCH.sub.3                                                                             OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                       H      O      CH.sub.3                                                                            Cl      OCH.sub.3.sup.b,d,f                    OSO.sub.2 CH.sub.3                                                                       H      O      CH.sub.3                                                                            OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CF.sub.3                                                                       H      O      H     CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                       H      O      H     CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                       H      O      H     OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                       H      O      CH.sub.3                                                                            OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCH.sub.3                                                                       H      O      CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               CH.sub.2 OCF.sub.2 H                                                                     H      O      H     OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                     H      O      H     OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCF.sub.2 H                                                                     H      O      CH.sub.3                                                                            Cl      OCH.sub.3.sup.b,d,f                    CH.sub.2 OCF.sub.2 H                                                                     H      O      CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3  H      S      H     CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3  H      S      H     OCH.sub.3                                                                             OCH.sub.3                              SCH.sub.3  H      S      CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3  H      S      CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               SCH.sub.2 CH.sub.3                                                                       H      S      H     CH.sub.3                                                                              OCH.sub.3                              SCH.sub.2 CH.sub.2 CH.sub.3                                                              H      S      H     CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                             H      S      H     CH.sub.3                                                                              CH.sub.3                               S(O)CH.sub.3                                                                             H      S      H     CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                             H      S      CH.sub.3                                                                            Cl      OCH.sub.3.sup.b,d,f                    S(O).sub.2 CH.sub.3                                                                      H      S      H     OCH.sub.3                                                                             OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                      H      S      H     CH.sub.3                                                                              OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                      H      S      CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3   H      S      H     CH.sub.3                                                                              CH.sub.3                               CF.sub.3   H      O      H     OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3   H      S      CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                        H      S      H     CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                        H      S      H     OCH.sub.3                                                                             OCH.sub.3                              N(CH.sub.3).sub.2                                                                        H      S      CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H      S      H     CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.2 CH.sub.3).sub.2                                                               H      S      H     OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        H      S      H     CH.sub.3                                                                              OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        H      S      H     OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        H      S      CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H      S      H     CH.sub.3                                                                              OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                               H      S      H     OCH.sub.3                                                                             OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                               H      S      CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                          H      S      H     CH.sub.3                                                                              CH.sub.3                               C.sub.6 H.sub.5                                                                          H      S      H     CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                          H      S      H     OCH.sub.3                                                                             OCH.sub.3                              C.sub.6 H.sub.5                                                                          H      S      CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 Cl                                                                    H      S      H     CH.sub.3                                                                              OCH.sub.3                              2'-C.sub.6 H.sub.4 CH.sub.3                                                              H      S      H     OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H      S      H     OCF.sub.2 H                                                                           OCH.sub.3                              3'-C.sub.6 H.sub.4 Br                                                                    H      S      H     CH.sub.3                                                                              OCH.sub.3                              4'-C.sub.6 H.sub.4 F                                                                     H      S      H     Cl      OCH.sub.3.sup.b,d,f                    CH.sub.2 CO.sub.2 CH.sub.3                                                               H      S      H     CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                               H      S      H     OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                               H      S      CH.sub.3                                                                            Cl      OCH.sub.3.sup.b,d,f                     ##STR93## H      S      H     OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CH.sub.3                                                                       H      S      H     CH.sub.3                                                                              OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                       H      S      H     OCH.sub.3                                                                             OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                       H      S      CH.sub.3                                                                            Cl      OCH.sub.3.sup.b,d,f                    OSO.sub.2 CH.sub.3                                                                       H      S      CH.sub.3                                                                            OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CF.sub.3                                                                       H      S      H     CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                       H      S      H     CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                       H      S      H     OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                       H      S      CH.sub.3                                                                            OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCH.sub.3                                                                       H      S      CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               CH.sub.2 OCF.sub.2 H                                                                     H      S      H     OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                     H      S      H     OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCF.sub.2 H                                                                     H      S      CH.sub.3                                                                            Cl      OCH.sub.3.sup.b,d,f                    CH.sub.2 OCF.sub.2 H                                                                     H      S      CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                         ##STR94##                                                                     ##STR95##                                                                    R.sub.1       R.sub.3                                                                              R.sub.15                                                                              X       Y                                        ______________________________________                                        SCH.sub.3     H      H       CH.sub.3                                                                              OCH.sub.3                                SCH.sub.3     H      H       OCH.sub.3                                                                             OCH.sub.3                                SCH.sub.3     H      CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                                SCH.sub.3     H      CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                 SCH.sub.2 CH.sub.3                                                                          H      H       CH.sub.3                                                                              OCH.sub.3                                SCH.sub.2 CH.sub.2 CH.sub.3                                                                 H      H       CH.sub.3                                                                              OCH.sub.3                                S(O)CH.sub.3  H      H       CH.sub.3                                                                              CH.sub.3                                 S(O)CH.sub.3  H      H       CH.sub.3                                                                              OCH.sub.3                                S(O)CH.sub.3  H      CH.sub.3                                                                              Cl      OCH.sub.3.sup.b,d                        S(O).sub.2 CH.sub.3                                                                         H      H       OCH.sub.3                                                                             OCH.sub.3                                S(O).sub.2 CH.sub.3                                                                         H      H       CH.sub.3                                                                              OCH.sub.3                                S(O).sub.2 CH.sub.3                                                                         H      CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                                CF.sub.3      H      H       CH.sub.3                                                                              CH.sub.3                                 CF.sub.3      H      H       OCH.sub.3                                                                             OCH.sub.3                                CF.sub.3      H      CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                                N(CH.sub.3).sub.2                                                                           H      H       CH.sub.3                                                                              OCH.sub.3                                N(CH.sub.3).sub.2                                                                           H      H       OCH.sub.3                                                                             OCH.sub.3                                N(CH.sub.3).sub.2                                                                           H      CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                                N(CH.sub.3)CH.sub.2 CH.sub.3                                                                H      H       CH.sub.3                                                                              OCH.sub.3                                N(CH.sub.2 CH.sub.3).sub. 2                                                                 H      H       OCH.sub.3                                                                             OCH.sub.3                                CO.sub.2 CH.sub.3                                                                           H      H       CH.sub.3                                                                              OCH.sub.3                                CO.sub.2 CH.sub.3                                                                           H      H       OCH.sub.3                                                                             OCH.sub.3                                CO.sub.2 CH.sub.3                                                                           H      CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                 CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                               H      H       CH.sub.3                                                                              OCH.sub.3                                SO.sub.2 N(CH.sub.3).sub.2                                                                  H      H       OCH.sub.3                                                                             OCH.sub.3                                SO.sub.2 N(CH.sub.3).sub.2                                                                  H      CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                                C.sub.6 H.sub.5                                                                             H      H       CH.sub.3                                                                              CH.sub.3                                 C.sub.6 H.sub.5                                                                             H      H       CH.sub.3                                                                              OCH.sub.3                                C.sub.6 H.sub.5                                                                             H      H       OCH.sub.3                                                                             OCH.sub.3                                C.sub.6 H.sub.5                                                                             H      CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                                2'-C.sub.6 H.sub.4 Cl                                                                       H      H       CH.sub.3                                                                              OCH.sub.3                                2'-C.sub.6 H.sub.4 CH.sub.3                                                                 H      H       OCH.sub.3                                                                             OCH.sub.3                                2'-C.sub.6 H.sub.4 OCH.sub.3                                                                H      H       OCF.sub.2 H                                                                           OCH.sub.3                                3'-C.sub.6 H.sub.4 Br                                                                       H      H       CH.sub.3                                                                              OCH.sub.3                                4'-C.sub.6 H.sub.4 F                                                                        H      H       Cl      OCH.sub.3.sup.b,d                        CH.sub.2 CO.sub.2 CH.sub.3                                                                  H      H       CH.sub.3                                                                              OCH.sub.3                                CH.sub.2 CO.sub.2 CH.sub.3                                                                  H      H       OCH.sub.3                                                                             OCH.sub.3                                CH.sub.2 CO.sub.2 CH.sub.3                                                                  H      CH.sub.3                                                                              Cl      OCH.sub.3.sup.b,d                         ##STR96##    H      H       OCH.sub.3                                                                             OCF.sub.2 H                              OSO.sub.2 CH.sub.3                                                                          H      H       CH.sub.3                                                                              OCH.sub.3                                OSO.sub.2 CH.sub.3                                                                          H      H       OCH.sub.3                                                                             OCH.sub.3                                OSO.sub.2 CH.sub.3                                                                          H      CH.sub.3                                                                              Cl      OCH.sub.3.sup.b,d                        OSO.sub.2 CH.sub.3                                                                          H      CH.sub.3                                                                              OCH.sub.3                                                                             OCF.sub.2 H                              OSO.sub.2 CF.sub.3                                                                          H      H       CH.sub.3                                                                              OCH.sub.3                                CH.sub.2 OCH.sub.3                                                                          H      H       CH.sub.3                                                                              OCH.sub.3                                CH.sub.2 OCH.sub.3                                                                          H      H       OCH.sub.3                                                                             OCH.sub.3                                CH.sub.2 OCH.sub.3                                                                          H      CH.sub.3                                                                              OCH.sub.3                                                                             OCF.sub.2 H                              CH.sub.2 OCH.sub.3                                                                          H      CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                 CH.sub.2 OCF.sub.2 H                                                                        H      H       OCH.sub.3                                                                             OCH.sub.3                                CH.sub.2 OCF.sub.2 H                                                                        H      H       OCH.sub.3                                                                             OCF.sub.2 H                              CH.sub.2 OCF.sub.2 H                                                                        H      CH.sub.3                                                                              Cl      OCH.sub.3.sup.b,d                        CH.sub.2 OCF.sub.2 H                                                                        H      CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                                ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                        (a.) Z = N (b.) Z = CH                                                                     ##STR97##                                                        (c.) Z = N (d.) Z = CH                                                                     ##STR98##                                                        (e.) Z = N (f.) Z = CH                                                                     ##STR99##                                                        R.sub.1    R.sub.3                                                                              W       R.sub.15                                                                           R.sub.16                                                                           X     Y                                   ______________________________________                                        SCH.sub.3  H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           SCH.sub.3  H      O       H    H    OCH.sub.3                                                                           OCH.sub.3                           SCH.sub.3  H      O       CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           SCH.sub.3  H      O       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           SCH.sub.3  H      O       CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                            SCH.sub.2 CH.sub.3                                                                       H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           SCH.sub.2 CH.sub.2 CH.sub.3                                                              H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           S(O)CH.sub.3                                                                             H      O       H    H    CH.sub.3                                                                            CH.sub.3                            S(O)CH.sub.3                                                                             H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           S(O)CH.sub.3                                                                             H      O       CH.sub.3                                                                           H    Cl    OCH.sub.3.sup.b,d,f                 S(O)CH.sub.3                                                                             H      O       H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H      O       H    H    OCH.sub.3                                                                           OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H      O       CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H      O       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           CF.sub.3   H      O       H    H    CH.sub.3                                                                            CH.sub.3                            CF.sub.3   H      O       CH.sub.3                                                                           H    OCH.sub.3                                                                           CH.sub.3                            CF.sub.3   H      O       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           CF.sub.3   H      O       CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      O       H    H    OCH.sub.3                                                                           OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      O       CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      O       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.2 CH.sub.3).sub.2                                                               H      O       H    H    OCH.sub.3                                                                           OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H      O       CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H      O       H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                            CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           SO.sub.2 N(CH.sub.3).sub.2                                                               H      O       H    H    OCH.sub.3                                                                           OCH.sub.3                           SO.sub.2 N(CH.sub.3).sub.2                                                               H      O       CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      O       H    H    CH.sub.3                                                                            CH.sub.3                            C.sub.6 H.sub.5                                                                          H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      O       H    H    OCH.sub.3                                                                           OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      O       CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      O       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      O       CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                         2'-C.sub.6 H.sub.4 Cl                                                                    H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H      O       H    H    OCH.sub.3                                                                           OCH.sub.3                           2'-C.sub.6 H.sub.4 CH.sub.3                                                              H      O       H    H    Cl    OCH.sub.3.sup.b,d,f                 3'-C.sub.6 H.sub.4 Br                                                                    H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           4'-C.sub.6 H.sub.4 F                                                                     H      O       H    H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 CO.sub.2 CH.sub.3                                                               H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 CO.sub.2 CH.sub.3                                                               H      O       CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 CO.sub.2 CH.sub.3                                                               H      O       H    CH.sub.3                                                                           Cl    OCH.sub.3.sup.b,d,f                  ##STR100##                                                                              H      O       H    H    OCH.sub.3                                                                           OCF.sub.2 H                         OSO.sub.2 CH.sub.3                                                                       H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           OSO.sub.2 CH.sub.3                                                                       H      O       CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           OSO.sub.2 CH.sub.3                                                                       H      O       H    CH.sub.3                                                                           Cl    OCH.sub.3.sup.b,d,f                 OSO.sub.2 CH.sub.3                                                                       H      O       CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                         OSO.sub.2 CF.sub.3                                                                       H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H      O       H    H    CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H      O       CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H      O       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub. 2 H                        CH.sub.2 OCH.sub.3                                                                       H      O       CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                            CH.sub.2 OCF.sub.2 H                                                                     H      O       H    H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 OCF.sub.2 H                                                                     H      O       CH.sub.3                                                                           H    OCH.sub.3                                                                           OCF.sub.2 H                         CH.sub.2 OCF.sub.2 H                                                                     H      O       H    CH.sub.3                                                                           Cl    OCH.sub.3.sup.b,d,f                 CH.sub.2 OCF.sub.2 H                                                                     H      O       CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           SCH.sub.3  H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           SCH.sub.3  H      NCH.sub.3                                                                             H    H    OCH.sub.3                                                                           OCH.sub.3                           SCH.sub.3  H      NCH.sub.3                                                                             CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           SCH.sub.3  H      NCH.sub.3                                                                             H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           SCH.sub.3  H      NH      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                            SCH.sub.2 CH.sub.3                                                                       H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           SCH.sub.2 CH.sub.2 CH.sub.3                                                              H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           S(O)CH.sub.3                                                                             H      NH      H    H    CH.sub.3                                                                            CH.sub.3                            S(O)CH.sub.3                                                                             H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           S(O)CH.sub.3                                                                             H      NCH.sub.3                                                                             CH.sub.3                                                                           H    Cl    OCH.sub.3.sup.b,d,f                 S(O)CH.sub.3                                                                             H      NCH.sub.3                                                                             H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H      NCH.sub.3                                                                             H    H    OCH.sub.3                                                                           OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H      NCH.sub.3                                                                             CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H      NCH.sub.3                                                                             H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           CF.sub.3   H      NH      H    H    CH.sub.3                                                                            CH.sub.3                            CF.sub.3   H      NCH.sub.3                                                                             CH.sub.3                                                                           H    OCH.sub.3                                                                           CH.sub.3                            CF.sub.3   H      NCH.sub.3                                                                             H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           CF.sub.3   H      NH      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      NCH.sub.3                                                                             H    H    OCH.sub.3                                                                           OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      NCH.sub.3                                                                             CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      NCH.sub.3                                                                             H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.2 CH.sub.3).sub.2                                                               H      NCH.sub.3                                                                             H    H    OCH.sub.3                                                                           OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H      NCH.sub.3                                                                             CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H      NCH.sub.3                                                                             H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                            CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           SO.sub.2 N(CH.sub.3).sub.2                                                               H      NCH.sub.3                                                                             H    H    OCH.sub.3                                                                           OCH.sub.3                           SO.sub.2 N(CH.sub.3).sub.2                                                               H      NH      CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            CH.sub.3                            C.sub.6 H.sub.5                                                                          H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      NCH.sub.3                                                                             H    H    OCH.sub.3                                                                           OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      NCH.sub.3                                                                             CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      NCH.sub.3                                                                             H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      NCH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                         2'-C.sub.6 H.sub.4 Cl                                                                    H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H      NCH.sub.3                                                                             H    H    OCH.sub.3                                                                           OCH.sub.3                           2'-C.sub.6 H.sub.4 CH.sub.3                                                              H      NCH.sub.3                                                                             H    H    Cl    OCH.sub.3.sup.b,d,f                 3'-C.sub.6 H.sub.4 Br                                                                    H      NH      H    H    CH.sub.3                                                                            OCH.sub.3                           4'-C.sub.6 H.sub.4 F                                                                     H      NCH.sub.3                                                                             H    H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 CO.sub.2 CH.sub.3                                                               H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 CO.sub.2 CH.sub.3                                                               H      NCH.sub.3                                                                             CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 CO.sub.2 CH.sub.3                                                               H      NCH.sub.3                                                                             H    CH.sub.3                                                                           Cl    OCH.sub.3.sup.b,d,f                  ##STR101##                                                                              H      NCH.sub.3                                                                             H    H    OCH.sub.3                                                                           OCF.sub.2 H                         OSO.sub.2 CH.sub.3                                                                       H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           OSO.sub.2 CH.sub.3                                                                       H      NCH.sub.3                                                                             CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           OSO.sub.2 CH.sub.3                                                                       H      NCH.sub.3                                                                             H    CH.sub.3                                                                           Cl    OCH.sub.3.sup.b,d,f                 OSO.sub.2 CH.sub.3                                                                       H      NCH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                         OSO.sub.2 CF.sub.3                                                                       H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H      NCH.sub.3                                                                             H    H    CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H      NCH.sub.3                                                                             CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H      NH      H    CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                         CH.sub.2 OCH.sub.3                                                                       H      NCH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                            CH.sub.2 OCF.sub.2 H                                                                     H      NCH.sub.3                                                                             H    H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 OCF.sub.2 H                                                                     H      NCH.sub.3                                                                             CH.sub.3                                                                           H    OCH.sub.3                                                                           OCF.sub.2 H                         CH.sub.2 OCF.sub.2 H                                                                     H      NCH.sub.3                                                                             H    CH.sub.3                                                                           Cl    OCH.sub.3.sup.b,d,f                 CH.sub.2 OCF.sub.2 H                                                                     H      NCH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           SCH.sub.3  H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           SCH.sub.3  H      S       H    H    OCH.sub.3                                                                           OCH.sub.3                           SCH.sub.3  H      S       CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           SCH.sub.3  H      S       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           SCH.sub.3  H      S       CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                            SCH.sub.3  3-Cl   S       CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           SCH.sub.2 CH.sub.3                                                                       H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           SCH.sub.2 CH.sub.2 CH.sub.3                                                              H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           S(O)CH.sub.3                                                                             H      S       H    H    CH.sub.3                                                                            CH.sub.3                            S(O)CH.sub.3                                                                             H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           S(O)CH.sub.3                                                                             H      S       CH.sub.3                                                                           H    Cl    OCH.sub.3.sup.b,d,f                 S(O)CH.sub.3                                                                             H      S       H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H      S       H    H    OCH.sub.3                                                                           OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H      S       CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H      S       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           CF.sub.3   H      S       H    H    CH.sub.3                                                                            CH.sub.3                            CF.sub.3   H      S       CH.sub.3                                                                           H    OCH.sub.3                                                                           CH.sub.3                            CF.sub.3   H      O       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           CF.sub.3   H      S       CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      S       H    H    OCH.sub.3                                                                           OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      S       CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H      S       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.2 CH.sub.3).sub.2                                                               H      S       H    H    OCH.sub.3                                                                           OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H      S       CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H      S       H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                            CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           SO.sub.2 N(CH.sub.3).sub.2                                                               H      S       H    H    OCH.sub.3                                                                           OCH.sub.3                           SO.sub.2 N(CH.sub.3).sub.2                                                               H      S       CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      S       H    H    CH.sub.3                                                                            CH.sub.3                            C.sub.6 H.sub.5                                                                          H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      S       H    H    OCH.sub.3                                                                           OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      S       CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      S       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           C.sub.6 H.sub.5                                                                          H      S       CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                         2'-C.sub.6 H.sub.4 Cl                                                                    H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H      S       H    H    OCH.sub.3                                                                           OCH.sub.3                           2'-C.sub.6 H.sub.4 CH.sub.3                                                              H      S       H    H    Cl    OCH.sub.3.sup.b,d,f                 3'-C.sub.6 H.sub.4 Br                                                                    H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           4'-C.sub.6 H.sub.4 F                                                                     H      S       H    H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 CO.sub.2 CH.sub.3                                                               H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 CO.sub.2 CH.sub.3                                                               H      S       CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 CO.sub.2 CH.sub.3                                                               H      S       H    CH.sub.3                                                                           Cl    OCH.sub.3.sup.b,d,f                  ##STR102##                                                                              H      S       H    H    OCH.sub.3                                                                           OCF.sub.2 H                         OSO.sub.2 CH.sub.3                                                                       H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           OSO.sub.2 CH.sub.3                                                                       H      S       CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           OSO.sub.2 CH.sub.3                                                                       H      S       H    CH.sub.3                                                                           Cl    OCH.sub.3.sup.b,d,f                 OSO.sub.2 CH.sub.3                                                                       H      S       CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                         OSO.sub.2 CF.sub.3                                                                       H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H      S       H    H    CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H      S       CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H      S       H    CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                         CH.sub.2 OCH.sub.3                                                                       H      S       CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                            CH.sub.2 OCF.sub.2 H                                                                     H      S       H    H    OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 OCF.sub.2 H                                                                     H      S       CH.sub.3                                                                           H    OCH.sub.3                                                                           OCF.sub.2 H                         CH.sub.2 OCF.sub.2 H                                                                     H      S       H    CH.sub.3                                                                           Cl    OCH.sub.3.sup.b,d,f                 CH.sub.2 OCF.sub.2 H                                                                     H      S       CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                        (a.) Z = N (b.) Z = CH                                                                     ##STR103##                                                       (c.) Z = N (d.) Z = CH                                                                     ##STR104##                                                       (e.) Z = N (f.) Z = CH                                                                     ##STR105##                                                       R.sub.1    R.sub.3                                                                              R.sub.19 R.sub.20                                                                             X     Y                                     ______________________________________                                        SCH.sub.3  H      H        H      CH.sub.3                                                                            OCH.sub.3                             SCH.sub.3  H      H        H      OCH.sub.3                                                                           OCH.sub.3                             SCH.sub.3  H      3-CH.sub.3                                                                             H      CH.sub.3                                                                            OCH.sub.3                             SCH.sub.3  H      4-CH.sub.3                                                                             H      CH.sub.3                                                                            CH.sub.3                              SCH.sub.2 CH.sub.3                                                                       H      H        H      CH.sub.3                                                                            OCH.sub.3                             SCH.sub.2 CH.sub.2 CH.sub.3                                                              H      H        H      CH.sub.3                                                                            OCH.sub.3                             S(O)CH.sub.3                                                                             H      H        H      CH.sub.3                                                                            CH.sub.3                              S(O)CH.sub.3                                                                             H      H        H      CH.sub.3                                                                            OCH.sub.3                             S(O)CH.sub.3                                                                             H      5-CH.sub.3                                                                             H      Cl.sup.b,d,f                                                                        OCH.sub.3                             S(O).sub.2 CH.sub.3                                                                      H      H        H      OCH.sub.3                                                                           OCH.sub.3                             S(O).sub.2 CH.sub.3                                                                      H      H        H      CH.sub.3                                                                            OCH.sub.3                             S(O).sub.2 CH.sub.3                                                                      H      6-CH.sub.3                                                                             H      OCH.sub.3                                                                           OCH.sub.3                             CF.sub.3   H      H        H      CH.sub.3                                                                            CH.sub.3                              CF.sub.3   H      H        H      OCH.sub.3                                                                           OCH.sub.3                             CF.sub.3   H      3-CH.sub.3                                                                             4-CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                             N(CH.sub.3).sub.2                                                                        H      H        H      CH.sub.3                                                                            OCH.sub.3                             N(CH.sub.3).sub.2                                                                        H      H        H      OCH.sub.3                                                                           OCH.sub.3                             N(CH.sub.3).sub.2                                                                        H      3-CH.sub.3                                                                             5-CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                             N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H      H        H      CH.sub.3                                                                            OCH.sub.3                             N(CH.sub.2 CH.sub.3).sub.2                                                               H      H        H      OCH.sub.3                                                                           OCH.sub.3                             CO.sub.2 CH.sub.3                                                                        H      H        H      CH.sub.3                                                                            OCH.sub.3                             CO.sub.2 CH.sub.3                                                                        H      H        H      OCH.sub.3                                                                           OCH.sub.3                             CO.sub.2 CH.sub.3                                                                        H      3-CH.sub.3                                                                             6-CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                              CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H      H        H      CH.sub.3                                                                            OCH.sub.3                             SO.sub.2 N(CH.sub.3).sub.2                                                               H      H        H      OCH.sub.3                                                                           OCH.sub.3                             SO.sub.2 N(CH.sub.3).sub.2                                                               H      4-CH.sub.3                                                                             5-CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                             C.sub.6 H.sub.5                                                                          H      H        H      CH.sub.3                                                                            CH.sub.3                              C.sub.6 H.sub.5                                                                          H      H        H      CH.sub.3                                                                            OCH.sub.3                             C.sub.6 H.sub.5                                                                          H      H        H      OCH.sub.3                                                                           OCH.sub.3                             C.sub.6 H.sub.5                                                                          H      4-CH.sub.3                                                                             6-CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                             2'-C.sub.6 H.sub.4 Cl                                                                    H      H        H      CH.sub.3                                                                            OCH.sub.3                             2'-C.sub.6 H.sub.4 CH.sub.3                                                              H      H        H      OCH.sub.3                                                                           OCH.sub.3                             2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H      H        H      OCF.sub.2 H                                                                         OCH.sub.3                             3'-C.sub.6 H.sub.4 Br                                                                    H      H        H      CH.sub.3                                                                            OCH.sub.3                             4'-C.sub.6 H.sub.4 F                                                                     H      H        H      Cl.sup.b,d,f                                                                        OCH.sub.3                             CH.sub.2 CO.sub.2 CH.sub.3                                                               H      H        H      CH.sub.3                                                                            OCH.sub.3                             CH.sub.2 CO.sub.2 CH.sub.3                                                               H      H        H      OCH.sub.3                                                                           OCH.sub.3                             CH.sub.2 CO.sub.2 CH.sub.3                                                               H      5-CH.sub.3                                                                             6-CH.sub.3                                                                           Cl.sup.b,d,f                                                                        OCH.sub.3                              ##STR106##                                                                              H      H        H      OCH.sub.3                                                                           OCF.sub.2 H                           OSO.sub.2 CH.sub.3                                                                       H      H        H      CH.sub.3                                                                            OCH.sub.3                             OSO.sub.2 CH.sub.3                                                                       H      H        H      OCH.sub.3                                                                           OCH.sub.3                             OSO.sub.2 CH.sub.3                                                                       H      6-CH.sub.3                                                                             H      Cl.sup.b,d,f                                                                        OCH.sub.3                             OSO.sub.2 CH.sub.3                                                                       H      3-CH.sub.3                                                                             H      OCH.sub.3                                                                           OCF.sub.2 H                           OSO.sub.2 CF.sub.3                                                                       H      H        H      CH.sub.3                                                                            OCH.sub.3                             CH.sub.2 OCH.sub.3                                                                       H      H        H      CH.sub.3                                                                            OCH.sub.3                             CH.sub.2 OCH.sub.3                                                                       H      H        H      OCH.sub.3                                                                           OCH.sub.3                             CH.sub.2 OCH.sub.3                                                                       H      6-CH.sub.3                                                                             H      OCH.sub.3                                                                           OCF.sub.2 H                           CH.sub.2 OCH.sub.3                                                                       H      3-CH.sub.3                                                                             H      CH.sub.3                                                                            CH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                     H      H        H      OCH.sub.3                                                                           OCH.sub.3                             CH.sub.2 OCF.sub.2 H                                                                     H      H        H      OCH.sub.3                                                                           OCF.sub.2 H                           CH.sub.2 OCF.sub.2 H                                                                     H      6-CH.sub.3                                                                             H      Cl.sup.b,d,f                                                                        OCH.sub.3                             CH.sub.2 OCF.sub.2 H                                                                     H      3-CH.sub.3                                                                             H      CH.sub.3                                                                            OCH.sub.3                             ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                         ##STR107##               (a.) Z = N (b.) Z = CH                              R.sub.1    R.sub.3                                                                             R.sub.21                                                                              R.sub.22                                                                           R.sub.23                                                                            X     Y                                   ______________________________________                                        SCH.sub.3  H     CH.sub.3                                                                              H    OCH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           SCH.sub.3  H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           SCH.sub.3  H     CH.sub.3                                                                              CH.sub.3                                                                           H     CH.sub.3                                                                            OCH.sub.3                           SCH.sub.3  H     H       CH.sub.3                                                                           H     OCH.sub.3                                                                           OCH.sub.3                           SCH.sub.3  H     CH.sub.3                                                                              CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                            SCH.sub.2 CH.sub.3                                                                       H     OCH.sub.3                                                                             H    OCH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                           SCH.sub.2 CH.sub.2 CH.sub.3                                                              H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           S(O)CH.sub.3                                                                             H     CH.sub.3                                                                              H    OCH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                            S(O)CH.sub.3                                                                             H     H       H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           S(O)CH.sub.3                                                                             H     CH.sub.3                                                                              H    CH.sub.3                                                                            Cl.sup.b                                                                            OCH.sub.3                           S(O)CH.sub.3                                                                             H     H       CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           S(O).sub.2 CH.sub.3                                                                      H     H       CH.sub.3                                                                           H     OCH.sub.3                                                                           OCH.sub.3                           CF.sub.3   H     OCH.sub.3                                                                             H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                            CF.sub.3   H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           CH.sub.3                            CF.sub.3   H     H       CH.sub.3                                                                           H     OCH.sub.3                                                                           OCH.sub.3                           CF.sub.3   H     CH.sub.3                                                                              CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H     H       CH.sub.3                                                                           CH.sub.3                                                                            CH.sub. 3                                                                           OCH.sub.3                           N(CH.sub.3).sub.2                                                                        H     H       CH.sub.3                                                                           H     OCH.sub.3                                                                           OCH.sub.3                           N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           N(CH.sub.2 CH.sub.3).sub.2                                                               H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H     H       CH.sub.3                                                                           H     CH.sub.3                                                                            CH.sub.3                            CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           SO.sub.2 N(CH.sub.3).sub.2                                                               H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           SO.sub.2 N(CH.sub.3).sub.2                                                               H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                            C.sub.6 H.sub.5                                                                          H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           C.sub.6 H.sub.5                                                                          H     CH.sub.3                                                                              CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           C.sub.6 H.sub.5                                                                          H     H       CH.sub.3                                                                           H     OCH.sub.3                                                                           OCH.sub.3                           2'-C.sub.6 H.sub.4 Cl                                                                    H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           3'-C.sub.6 H.sub.4 Br                                                                    H     CH.sub.3                                                                              H    OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                           4'-C.sub.6 H.sub.4 F                                                                     H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           2'-C.sub.6 H.sub.4 CH.sub.3                                                              H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCF.sub.2 H                         CH.sub.2 CO.sub.2 CH.sub.3                                                               H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 CO.sub.2 CH.sub.3                                                               H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 CO.sub.2 CH.sub.3                                                               H     H       CH.sub.3                                                                           CH.sub.3                                                                            Cl.sup.b                                                                            OCH.sub.3                            ##STR108##                                                                              H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCF.sub.2 H                         OSO.sub.2 CH.sub.3                                                                       H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           OSO.sub.2 CH.sub.3                                                                       H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           OSO.sub.2 CH.sub.3                                                                       H     H       CH.sub.3                                                                           H     Cl.sup. b                                                                           OCH.sub.3                           OSO.sub.2 CH.sub.3                                                                       H     CH.sub.3                                                                              CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                                                           OCF.sub.2 H                         OSO.sub.2 CF.sub.3                                                                       H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H     CH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 OCH.sub.3                                                                       H     H       CH.sub.3                                                                           H     OCH.sub.3                                                                           OCF.sub.2 H                         CH.sub.2 OCH.sub.3                                                                       H     CH.sub.3                                                                              CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                            CH.sub.2 OCF.sub.2 H                                                                     H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCH.sub.3                           CH.sub.2 OCF.sub.2 H                                                                     H     CH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                           OCF.sub.2 H                         CH.sub.2 OCF.sub.2 H                                                                     H     H       CH.sub.3                                                                           H     Cl.sup.b                                                                            OCH.sub.3                           CH.sub.2 OCF.sub.2 H                                                                     H     CH.sub.3                                                                              CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                           ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                         ##STR109##               (a.) Z = N (b.) Z = CH                              R.sub.1    R.sub.3                                                                              R.sub.24                                                                              R.sub.25                                                                             X      Y                                     ______________________________________                                        SCH.sub.3  H      H       H      CH.sub.3                                                                             OCH.sub.3                             SCH.sub.3  H      H       H      OCH.sub.3                                                                            OCH.sub.3                             SCH.sub.3  H      3-CH.sub.3                                                                            H      CH.sub.3                                                                             OCH.sub.3                             SCH.sub.3  H      3-CH.sub.3                                                                            H      CH.sub.3                                                                             CH.sub.3                              SCH.sub.2 CH.sub.3                                                                       H      H       H      CH.sub.3                                                                             OCH.sub.3                             SCH.sub.2 CH.sub.2 CH.sub.3                                                              H      H       H      CH.sub.3                                                                             OCH.sub.3                             S(O)CH.sub.3                                                                             H      H       H      CH.sub.3                                                                             CH.sub.3                              S(O)CH.sub.3                                                                             H      H       H      CH.sub.3                                                                             OCH.sub.3                             S(O)CH.sub.3                                                                             H      5-CH.sub.3                                                                            H      Cl.sup.b                                                                             OCH.sub.3                             S(O).sub.2 CH.sub.3                                                                      H      H       H      OCH.sub.3                                                                            OCH.sub.3                             S(O).sub.2 CH.sub.3                                                                      H      H       H      CH.sub.3                                                                             OCH.sub.3                             S(O).sub.2 CH.sub.3                                                                      H      6-CH.sub.3                                                                            H      OCH.sub.3                                                                            OCH.sub.3                             CF.sub.3   H      H       H      CH.sub.3                                                                             CH.sub.3                              CF.sub.3   H      H       H      OCH.sub.3                                                                            OCH.sub.3                             CF.sub.3   H      3-CH.sub.3                                                                            5-CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                             N(CH.sub.3).sub.2                                                                        H      H       H      CH.sub.3                                                                             OCH.sub.3                             N(CH.sub.3).sub.2                                                                        H      H       H      OCH.sub.3                                                                            OCH.sub.3                             N(CH.sub.3).sub.2                                                                        H      3-CH.sub.3                                                                            6-CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                             N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H      H       H      CH.sub.3                                                                             OCH.sub.3                             N(CH.sub.2 CH.sub.3).sub.2                                                               H      H       H      OCH.sub.3                                                                            OCH.sub.3                             CO.sub.2 CH.sub.3                                                                        H      H       H      CH.sub.3                                                                             OCH.sub.3                             CO.sub.2 CH.sub.3                                                                        H      H       H      OCH.sub.3                                                                            OCH.sub.3                             CO.sub.2 CH.sub.3                                                                        H      5-CH.sub.3                                                                            6-CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                              CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H      H       H      CH.sub.3                                                                             OCH.sub.3                             SO.sub.2 N(CH.sub.3).sub.2                                                               H      H       H      OCH.sub.3                                                                            OCH.sub.3                             SO.sub.2 N(CH.sub.3).sub.2                                                               H      3-CH.sub.3                                                                            6-CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                             C.sub.6 H.sub.5                                                                          H      H       H      CH.sub.3                                                                             CH.sub.3                              C.sub.6 H.sub.5                                                                          H      H       H      CH.sub.3                                                                             OCH.sub.3                             C.sub.6 H.sub.5                                                                          H      H       H      OCH.sub.3                                                                            OCH.sub.3                             C.sub.6 H.sub.5                                                                          H      5-CH.sub.3                                                                            6-CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                             2'-C.sub.6 H.sub.4 Cl                                                                    H      H       H      CH.sub.3                                                                             OCH.sub.3                             2'-C.sub.6 H.sub.4 CH.sub.3                                                              H      H       H      OCH.sub.3                                                                            OCH.sub.3                             2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H      H       H      OCF.sub.2 H                                                                          OCH.sub.3                             3'-C.sub.6 H.sub.4 Br                                                                    H      H       H      CH.sub.3                                                                             OCH.sub.3                             4'-C.sub.6 H.sub.4 F                                                                     H      H       H      Cl.sup.b                                                                             OCH.sub.3                             CH.sub.2 CO.sub.2 CH.sub.3                                                               H      H       H      CH.sub.3                                                                             OCH.sub.3                             CH.sub.2 CO.sub.2 CH.sub.3                                                               H      H       H      OCH.sub.3                                                                            OCH.sub.3                             CH.sub.2 CO.sub.2 CH.sub.3                                                               H      3-CH.sub.3                                                                            5-CH.sub.3                                                                           Cl.sup.b                                                                             OCH.sub.3                              ##STR110##                                                                              H      H       H      OCH.sub.3                                                                            OCF.sub.2 H                           OSO.sub.2 CH.sub. 3                                                                      H      H       H      CH.sub.3                                                                             OCH.sub.3                             OSO.sub.2 CH.sub.3                                                                       H      H       H      OCH.sub.3                                                                            OCH.sub.3                             OSO.sub.2 CH.sub.3                                                                       H      6-CH.sub.3                                                                            H      Cl.sup.b                                                                             OCH.sub.3                             OSO.sub.2 CH.sub.3                                                                       H      6-CH.sub.3                                                                            H      OCH.sub.3                                                                            OCF.sub.2 H                           OSO.sub.2 CF.sub.3                                                                       H      H       H      CH.sub.3                                                                             OCH.sub.3                             CH.sub.2 OCH.sub.3                                                                       H      H       H      CH.sub.3                                                                             OCH.sub.3                             CH.sub.2 OCH.sub.3                                                                       H      H       H      OCH.sub.3                                                                            OCH.sub.3                             CH.sub.2 OCH.sub.3                                                                       H      5-CH.sub.3                                                                            H      OCH.sub.3                                                                            OCF.sub.2 H                           CH.sub.2 OCH.sub.3                                                                       H      6-CH.sub.3                                                                            H      CH.sub.3                                                                             CH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                     H      H       H      OCH.sub.3                                                                            OCH.sub.3                             CH.sub.2 OCF.sub.2 H                                                                     H      H       H      OCH.sub.3                                                                            OCF.sub.2 H                           CH.sub.2 OCF.sub.2 H                                                                     H      5-CH.sub.3                                                                            H      Cl.sup.b                                                                             OCH.sub.3                             CH.sub.2 OCF.sub.2 H                                                                     H      6-CH.sub.3                                                                            H      CH.sub.3                                                                             OCH.sub.3                             ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                         ##STR111##                                                                   R.sub.1    R.sub.3                                                                             R.sub.21                                                                              R.sub.23                                                                            X       Y                                      ______________________________________                                        SCH.sub.3  H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3  H     H       H     OCH.sub.3                                                                             OCH.sub.3                              SCH.sub.3  H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3  H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               SCH.sub.2 CH.sub.3                                                                       H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              SCH.sub.2 CH.sub.2 CH.sub.3                                                              H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                             H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               S(O)CH.sub. 3                                                                            H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                             H     CH.sub.3                                                                              OCH.sub.3                                                                           Cl.sup.b                                                                              OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                      H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                      H     H       CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                      H     OCH.sub.3                                                                             OCH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3   H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               CF.sub.3   H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3   H     OCH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                        H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                        H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              N(CH.sub.3).sub.2                                                                        H     CH.sub.3                                                                              OCH.sub.3                                                                           CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.2 CH.sub.3).sub.2                                                               H     H       H     OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        H     H       OCH.sub.3                                                                           CH.sub.3                                                                              OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                        H     OCH.sub.3                                                                             OCH.sub.3                                                                           CH.sub.3                                                                              CH.sub.3                               CO.sub.2 CH.sub. 2 CH.sub.2 Cl                                                           H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                               H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                               H     OCH.sub.3                                                                             OCH.sub.3                                                                           CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                          H     H       OCH.sub.3                                                                           CH.sub.3                                                                              CH.sub.3                               C.sub.6 H.sub.5                                                                          H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                          H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              C.sub.6 H.sub.5                                                                          H     CH.sub.3                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 Cl                                                                    H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              2'-C.sub.6 H.sub.4 CH.sub.3                                                              H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H     H       CH.sub.3                                                                            OCF.sub.2 H                                                                           OCH.sub.3                              3'-C.sub.6 H.sub.4 Br                                                                    H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              4'-C.sub.6 H.sub.4 F                                                                     H     CH.sub.3                                                                              CH.sub.3                                                                            Cl.sup.b                                                                              OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                               H     OCH.sub.3                                                                             OCH.sub.3                                                                           CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                               H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub. 3                             CH.sub.2 CO.sub.2 CH.sub.3                                                               H     CH.sub.3                                                                              CH.sub.3                                                                            Cl      OCH.sub.3.sup.b                         ##STR112##                                                                              H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CH.sub.3                                                                       H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                       H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                       H     OCH.sub.3                                                                             H     Cl.sup.b                                                                              OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                       H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CF.sub.3                                                                       H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                       H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                       H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                       H     CH.sub.3                                                                              H     OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCH.sub.3                                                                       H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               CH.sub.2 OCF.sub.2 H                                                                     H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                     H     CH.sub.3                                                                              CH.sub.3                                                                            OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCF.sub.2 H                                                                     H     CH.sub.3                                                                              H     Cl.sup.b                                                                              OCH.sub.3                              CH.sub.2 OCF.sub. 2 H                                                                    H     CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              ______________________________________                                         .sup.a Z = N                                                                  .sup.b Z = CH                                                            

                  TABLE 13                                                        ______________________________________                                         ##STR113##                                                                   R.sub.1    R.sub.3                                                                             W'    R.sub.26                                                                           R.sub.27                                                                           R.sub.28                                                                           X     Y                                 ______________________________________                                        SCH.sub.3  H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         SCH.sub.3  H     O     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         SCH.sub.3  H     O     CH.sub.3                                                                           H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         SCH.sub.3  H     O     H    CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                         SCH.sub.3  H     O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                          SCH.sub.2 CH.sub.3                                                                       H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         SCH.sub.2 CH.sub.2 CH.sub.3                                                              H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         S(O)CH.sub.3                                                                             H     O     H    H    H    CH.sub.3                                                                            CH.sub.3                          S(O)CH.sub.3                                                                             H     O     H    H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         S(O)CH.sub.3                                                                             H     O     CH.sub.3                                                                           H    CH.sub.3                                                                           Cl.sup.b                                                                            OCH.sub.3                         S(O)CH.sub.3                                                                             H     O     H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         S(O).sub.2 CH.sub.3                                                                      H     O     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         S(O).sub.2 CH.sub.3                                                                      H     O     CH.sub.3                                                                           H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         S(O).sub.2 CH.sub.3                                                                      H     O     H    CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                         CF.sub.3   H     O     H    H    H    CH.sub.3                                                                            CH.sub.3                          CF.sub.3   H     O     CH.sub.3                                                                           H    H    OCH.sub.3                                                                           CH.sub.3                          CF.sub.3   H     O     H    CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                         CF.sub.3   H     O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         N(CH.sub.3).sub.2                                                                        H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         N(CH.sub.3).sub.2                                                                        H     O     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         N(CH.sub.3).sub.2                                                                        H     O     CH.sub.3                                                                           H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         N(CH.sub.3).sub.2                                                                        H     O     H    CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                         N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         N(CH.sub.2 CH.sub.3).sub.2                                                               H     O     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H     O     CH.sub.3                                                                           H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H     O     H    CH.sub.3                                                                           H    CH.sub.3                                                                            CH.sub.3                          CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         SO.sub.2 N(CH.sub.3).sub.2                                                               H     O     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         SO.sub.2 N(CH.sub.3).sub.2                                                               H     O     CH.sub.3                                                                           H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         C.sub.6 H.sub.5                                                                          H     O     H    H    H    CH.sub.3                                                                            CH.sub.3                          C.sub.6 H.sub.5                                                                          H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         C.sub.6 H.sub.5                                                                          H     O     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         C.sub.6 H.sub.5                                                                          H     O     CH.sub.3                                                                           H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         C.sub.6 H.sub.5                                                                          H     O     H    CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                         2'-C.sub.6 H.sub.4 Cl                                                                    H     O     H    H    H    CH.sub. 3                                                                           OCH.sub.3                         2'-C.sub.6 H.sub.4 Br                                                                    H     O     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         2'-C.sub.6 H.sub.4 F                                                                     H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         3'-C.sub.6 H.sub.4 CH.sub.3                                                              H     O     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         4'-C.sub.6 H.sub.4 OCH.sub.3                                                             H     O     H    H    H    OCH.sub.3                                                                           OCF.sub.2 H                       CH.sub.2 CO.sub.2 CH.sub.3                                                               H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         CH.sub.2 CO.sub.2 CH.sub.3                                                               H     O     CH.sub.3                                                                           H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                         CH.sub.2 CO.sub.2 CH.sub.3                                                               H     O     H    CH.sub.3                                                                           CH.sub.3                                                                           Cl.sup.b                                                                            OCH.sub.3                          ##STR114##                                                                              H     O     H    H    H    OCH.sub.3                                                                           OCF.sub.2 H                       OSO.sub.2 CH.sub.3                                                                       H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         OSO.sub.2 CH.sub.3                                                                       H     O     CH.sub.3                                                                           H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                         OSO.sub.2 CH.sub.3                                                                       H     O     H    CH.sub.3                                                                           H    Cl.sup.b                                                                            OCH.sub.3                         OSO.sub.2 CH.sub.3                                                                       H     O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                       OSO.sub.2 CF.sub.3                                                                       H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         CH.sub.2 OCH.sub.3                                                                       H     O     H    H    H    CH.sub.3                                                                            OCH.sub.3                         CH.sub.2 OCH.sub.3                                                                       H     O     CH.sub.3                                                                           H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                         CH.sub.2 OCH.sub.3                                                                       H     O     H    CH.sub.3                                                                           H    OCH.sub.3                                                                           OCF.sub.2 H                       CH.sub.2 OCH.sub.3                                                                       H     O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                          CH.sub.2 OCF.sub.2 H                                                                     H     O     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         CH.sub.2 OCF.sub.2 H                                                                     H     O     CH.sub.3                                                                           H    CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                       CH.sub.2 OCF.sub.2 H                                                                     H     O     H    CH.sub.3                                                                           H    Cl.sup.b                                                                            OCH.sub.3                         CH.sub.2 OCF.sub.2 H                                                                     H     O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         SCH.sub.3  H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         SCH.sub.3  H     S     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         SCH.sub.3  H     S     CH.sub.3                                                                           H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         SCH.sub.3  H     S     H    CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                         SCH.sub.3  H     S     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                          SCH.sub.2 CH.sub.3                                                                       H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         SCH.sub.2 CH.sub.2 CH.sub.3                                                              H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         S(O)CH.sub.3                                                                             H     S     H    H    H    CH.sub.3                                                                            CH.sub.3                          S(O)CH.sub.3                                                                             H     S     H    H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         S(O)CH.sub.3                                                                             H     S     CH.sub.3                                                                           H    CH.sub.3                                                                           Cl.sup.b                                                                            OCH.sub.3                         S(O)CH.sub.3                                                                             H     S     H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         S(O).sub.2 CH.sub.3                                                                      H     S     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         S(O).sub.2 CH.sub.3                                                                      H     S     CH.sub.3                                                                           H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         S(O).sub.2 CH.sub.3                                                                      H     S     H    CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                         CF.sub.3   H     S     H    H    H    CH.sub.3                                                                            CH.sub.3                          CF.sub.3   H     S     CH.sub.3                                                                           H    H    OCH.sub.3                                                                           CH.sub.3                          CF.sub.3   H     S     H    CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                         CF.sub.3   H     S     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         N(CH.sub.3).sub.2                                                                        H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         N(CH.sub.3).sub.2                                                                        H     S     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         N(CH.sub.3).sub.2                                                                        H     S     CH.sub.3                                                                           H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub. 3                        N(CH.sub.3).sub.2                                                                        H     S     H    CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                         N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         N(CH.sub.2 CH.sub.3).sub.2                                                               H     S     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H     S     CH.sub.3                                                                           H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H     S     H    CH.sub.3                                                                           H    CH.sub.3                                                                            CH.sub.3                          CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         SO.sub.2 N(CH.sub.3).sub.2                                                               H     S     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         SO.sub.2 N(CH.sub.3).sub.2                                                               H     S     CH.sub.3                                                                           H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         C.sub.6 H.sub.5                                                                          H     S     H    H    H    CH.sub.3                                                                            CH.sub.3                          C.sub.6 H.sub.5                                                                          H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         C.sub.6 H.sub.5                                                                          H     S     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         C.sub.6 H.sub.5                                                                          H     S     CH.sub.3                                                                           H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         C.sub.6 H.sub.5                                                                          H     S     H    CH.sub.3                                                                           H    OCH.sub. 3                                                                          OCH.sub.3                         2'-C.sub.6 H.sub.4 Cl                                                                    H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         2'-C.sub.6 H.sub.4 Br                                                                    H     S     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         2'-C.sub.6 H.sub.4 F                                                                     H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         3'-C.sub.6 H.sub.4 CH.sub.3                                                              H     S     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         4'-C.sub.6 H.sub.4 OCH.sub.3                                                             H     S     H    H    H    OCH.sub.3                                                                           OCF.sub.2 H                       CH.sub.2 CO.sub.2 CH.sub.3                                                               H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         CH.sub.2 CO.sub.2 CH.sub.3                                                               H     S     CH.sub.3                                                                           H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                         CH.sub.2 CO.sub.2 CH.sub.3                                                               H     S     H    CH.sub.3                                                                           CH.sub.3                                                                           Cl.sup.b                                                                            OCH.sub.3                          ##STR115##                                                                              H     S     H    H    H    OCH.sub.3                                                                           OCF.sub.2 H                       OSO.sub.2 CH.sub.3                                                                       H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         OSO.sub.2 CH.sub.3                                                                       H     S     CH.sub.3                                                                           H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                         OSO.sub.2 CH.sub.3                                                                       H     S     H    CH.sub.3                                                                           H    Cl.sup.b                                                                            OCH.sub.3                         OSO.sub.2 CH.sub.3                                                                       H     S     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                       OSO.sub.2 CF.sub.3                                                                       H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         CH.sub.2 OCH.sub.3                                                                       H     S     H    H    H    CH.sub.3                                                                            OCH.sub.3                         CH.sub.2 OCH.sub.3                                                                       H     S     CH.sub.3                                                                           H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                         CH.sub.2 OCH.sub.3                                                                       H     S     H    CH.sub.3                                                                           H    OCH.sub.3                                                                           OCF.sub.2 H                       CH.sub.2 OCH.sub.3                                                                       H     S     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                          CH.sub.2 OCF.sub.2 H                                                                     H     S     H    H    H    OCH.sub.3                                                                           OCH.sub.3                         CH.sub.2 OCF.sub.2 H                                                                     H     S     CH.sub.3                                                                           H    CH.sub.3                                                                           OCH.sub.3                                                                           OCF.sub.2 H                       CH.sub.2 OCF.sub.2 H                                                                     H     S     H    CH.sub.3                                                                           H    Cl.sup.b                                                                            OCH.sub.3                         CH.sub.2 OCF.sub.2 H                                                                     H     S     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                         ______________________________________                                         .sup.a Z = N                                                                  .sup.b Z = CH                                                            

                                      TABLE 14                                    __________________________________________________________________________     ##STR116##                                                                   R.sub.1  R.sub.3                                                                         W'                                                                              R.sub.26                                                                         R.sub.27                                                                         R.sub.28                                                                         R.sub.29                                                                         R.sub.30                                                                         R.sub.31                                                                         X    Y                                         __________________________________________________________________________    SCH.sub.3                                                                              H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 SCH.sub.3                                                                              H O H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 SCH.sub.3                                                                              H O CH.sub.3                                                                         H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 SCH.sub.3                                                                              H O H  H  CH.sub.3                                                                         H  H  H  Cl.sup.b                                                                           OCH.sub. 3                                SCH.sub.3                                                                              H O H  H  H  H  CH.sub.3                                                                         H  CH.sub.3                                                                           CH.sub.3                                  SCH.sub.2 CH.sub.3                                                                     H O CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                 SCH.sub.2 CH.sub.2 CH.sub.3                                                            H O H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 S(O)CH.sub.3                                                                           H O CH.sub.3                                                                         H  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                 S(O)CH.sub.3                                                                           H O CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                 S(O)CH.sub.3                                                                           H O H  H  H  H  H  H  Cl.sup.b                                                                           OCH.sub.3                                 S(O)CH.sub.3                                                                           H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 S(O).sub.2 CH.sub.3                                                                    H O H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 S(O).sub.2 CH.sub.3                                                                    H O CH.sub.3                                                                         CH.sub.3                                                                         H  H  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                 S(O).sub.2 CH.sub.3                                                                    H O H  H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  OCH.sub.3                                                                          OCH.sub.3                                 CF.sub.3 H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 CF.sub.3 H O CH.sub.3                                                                         H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 CF.sub. 3                                                                              H O H  H  CH.sub.3                                                                         H  H  H  Cl.sup.b                                                                           OCH.sub.3                                 CF.sub.3 H O H  H  H  H  CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                 N(CH.sub.3).sub.2                                                                      H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 N(CH.sub.3).sub.2                                                                      H O H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 N(CH.sub.3).sub.2                                                                      H O H  H  H  H  H  H  Cl.sup.b                                                                           OCH.sub.3                                 N(CH.sub.3).sub.2                                                                      H O CH.sub.3                                                                         H  H  H  H  CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                 N(CH.sub.3)CH.sub.2 CH.sub.3                                                           H O H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 N(CH.sub.2 CH.sub.3).sub.2                                                             H O H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 CO.sub.2 CH.sub.3                                                                      H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 CO.sub.2 CH.sub.3                                                                      H O H  H  CH.sub.3                                                                         H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 CO.sub.2 CH.sub.3                                                                      H O H  H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  CH.sub.3                                                                           CH.sub.3                                  CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                          H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub. 3                                SO.sub.2 N(CH.sub.3).sub.2                                                             H O H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 SO.sub.2 N(CH.sub.3).sub.2                                                             H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 C.sub.6 H.sub.5                                                                        H O H  H  H  H  H  H  CH.sub.3                                                                           CH.sub.3                                  C.sub.6 H.sub.5                                                                        H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 C.sub.6 H.sub.5                                                                        H O H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 C.sub.6 H.sub.5                                                                        H O CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                 C.sub.6 H.sub.5                                                                        H O CH.sub.3                                                                         H  H  H  CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                 2'-C.sub.6 H.sub.4 Cl                                                                  H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 2'-C.sub.6 H.sub.4 Br                                                                  H O CH.sub.3                                                                         H  CH.sub.3                                                                         H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 2'-C.sub.6 H.sub.4 F                                                                   H O H  H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                 3'-C.sub.6 H.sub.4 CH.sub.3                                                            H O H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 4' -C.sub.6 H.sub.4 OCH.sub.3                                                          H O H  H  H  H  H  H  OCF.sub.2 H                                                                        OCH.sub.3                                 CH.sub.2 CO.sub.2 CH.sub.3                                                             H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 CH.sub.2 CO.sub.2 CH.sub.3                                                             H O H  H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  OCH.sub.3                                                                          OCH.sub.3                                 CH.sub.2 CO.sub.2 CH.sub.3                                                             H O H  H  H  H  H  H  Cl.sup.b                                                                           OCH.sub.3                                  ##STR117##                                                                            H O H  H  H  H  H  H  OCF.sub.2 H                                                                        OCH.sub.3                                 OSO.sub.2 CH.sub.3                                                                     H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 OSO.sub.2 CH.sub.3                                                                     H O H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 OSO.sub.2 CH.sub.3                                                                     H O H  H  H  H  H  H  Cl.sup.b                                                                           OCH.sub.3                                 OSO.sub.2 CH.sub.3                                                                     H O H  H  H  H  H  H  OCF.sub.2 H                                                                        OCH.sub.3                                 OSO.sub.2 CF.sub.3                                                                     H O H  H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                 CH.sub.2 OCH.sub.3                                                                     H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 CH.sub. 2 OCH.sub.3                                                                    H O H  H  H  H  H  H  CH.sub.3                                                                           CH.sub.3                                  CH.sub.2 OCH.sub.3                                                                     H O H  H  CH.sub.3                                                                         H  H  H  OCF.sub.2 H                                                                        OCH.sub.3                                 CH.sub.2 OCH.sub.3                                                                     H O H  H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                           CH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                   H O H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 CH.sub.2 OCF.sub.2 H                                                                   H O H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 CH.sub.2 OCF.sub.2 H                                                                   H O CH.sub.3                                                                         H  H  H  CH.sub.3                                                                         H  Cl.sup.b                                                                           OCH.sub.3                                 CH.sub.2 OCF.sub.2 H                                                                   H O CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                 SCH.sub.3                                                                              H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 SCH.sub.3                                                                              H S H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 SCH.sub.3                                                                              H S CH.sub.3                                                                         H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 SCH.sub.3                                                                              H S H  H  CH.sub.3                                                                         H  H  H  Cl.sup.b                                                                           OCH.sub.3                                 SCH.sub.3                                                                              H S H  H  H  H  CH.sub.3                                                                         H  CH.sub.3                                                                           CH.sub.3                                  SCH.sub.2 CH.sub.3                                                                     H S CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                 SCH.sub.2 CH.sub.2 CH.sub.3                                                            H S H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 S(O)CH.sub.3                                                                           H S CH.sub.3                                                                         H  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                 S(O)CH.sub.3                                                                           H S CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                 S(O)CH.sub.3                                                                           H S H  H  H  H  H  H  Cl.sup.b                                                                           OCH.sub.3                                 S(O)CH.sub.3                                                                           H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 S(O).sub.2 CH.sub.3                                                                    H S H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 S(O).sub.2 CH.sub.3                                                                    H S CH.sub.3                                                                         CH.sub.3                                                                         H  H  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                 S(O).sub.2 CH.sub.3                                                                    H S H  H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  OCH.sub.3                                                                          OCH.sub.3                                 CF.sub.3 H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 CF.sub.3 H S CH.sub.3                                                                         H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 CF.sub.3 H S H  H  CH.sub.3                                                                         H  H  H  Cl.sup.b                                                                           OCH.sub.3                                 CF.sub.3 H S H  H  H  H  CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                 N(CH.sub.3).sub.2                                                                      H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 N(CH.sub.3).sub.2                                                                      H S H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 N(CH.sub.3).sub.2                                                                      H S H  H  H  H  H  H  Cl.sup.b                                                                           OCH.sub.3                                 N(CH.sub.3).sub.2                                                                      H S CH.sub.3                                                                         H  H  H  H  CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                 N(CH.sub.3)CH.sub.2 CH.sub.3                                                           H S H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 N(CH.sub.2 CH.sub.3).sub.2                                                             H S H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 CO.sub.2 CH.sub.3                                                                      H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 CO.sub.2 CH.sub.3                                                                      H S H  H  CH.sub.3                                                                         H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 CO.sub.2 CH.sub.3                                                                      H S H  H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  CH.sub.3                                                                           CH.sub.3                                  CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                          H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 SO.sub.2 N(CH.sub.3).sub.2                                                             H S H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub. 3                                SO.sub.2 N(CH.sub.3).sub.2                                                             H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 C.sub.6 H.sub.5                                                                        H S H  H  H  H  H  H  CH.sub.3                                                                           CH.sub.3                                  C.sub.6 H.sub.5                                                                        H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 C.sub.6 H.sub.5                                                                        H S H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 C.sub.6 H.sub.5                                                                        H S CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                 C.sub.6 H.sub.5                                                                        H S CH.sub.3                                                                         H  H  H  CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                 2'-C.sub.6 H.sub.4 Cl                                                                  H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 2'-C.sub.6 H.sub.4 Br                                                                  H S CH.sub.3                                                                         H  CH.sub.3                                                                         H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 2'-C.sub.6 H.sub.4 F                                                                   H S H  H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                 3'-C.sub.6 H.sub.4 CH.sub.3                                                            H S H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 4'-C.sub.6 H.sub.4 OCH.sub.3                                                           H S H  H  H  H  H  H  OCF.sub.2 H                                                                        OCH.sub.3                                 CH.sub.2 CO.sub.2 CH.sub.3                                                             H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 CH.sub.2 CO.sub.2 CH.sub.3                                                             H S H  H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  OCH.sub.3                                                                          OCH.sub.3                                 CH.sub.2 CO.sub.2 CH.sub.3                                                             H S H  H  H  H  H  H  Cl.sup.b                                                                           OCH.sub.3                                  ##STR118##                                                                            H S H  H  H  H  H  H  OCF.sub.2 H                                                                        OCH.sub.3                                 OSO.sub.2 CH.sub.3                                                                     H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 OSO.sub.2 CH.sub.3                                                                     H S H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 OSO.sub.2 CH.sub.3                                                                     H S H  H  H  H  H  H  Cl.sup.b                                                                           OCH.sub.3                                 OSO.sub.2 CH.sub.3                                                                     H S H  H  H  H  H  H  OCF.sub.2 H                                                                        OCH.sub.3                                 OSO.sub.2 CF.sub.3                                                                     H S H  H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                 CH.sub.2 OCH.sub.3                                                                     H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 CH.sub.2 OCH.sub.3                                                                     H S H  H  H  H  H  H  CH.sub.3                                                                           CH.sub.3                                  CH.sub.2 OCH.sub.3                                                                     H S H  H  CH.sub.3                                                                         H  H  H  OCF.sub.2 H                                                                        OCH.sub.3                                 CH.sub.2 OCH.sub.3                                                                     H S H  H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                           CH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                   H S H  H  H  H  H  H  CH.sub.3                                                                           OCH.sub.3                                 CH.sub.2 OCF.sub.2 H                                                                   H S H  H  H  H  H  H  OCH.sub.3                                                                          OCH.sub.3                                 CH.sub.2 OCF.sub.2 H                                                                   H S CH.sub.3                                                                         H  H  H  CH.sub.3                                                                         H  Cl.sup.b                                                                           OCH.sub.3                                 CH.sub.2 OCF.sub.2 H                                                                   H S CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                 __________________________________________________________________________     .sup.a Z = N                                                                  .sup.b Z = CH                                                            

                  TABLE 15                                                        ______________________________________                                         ##STR119##                                                                   In the following Table, R.sub.15 -R.sub.31 are H.                             Q        Q'        R.sub.3  X        Y                                        ______________________________________                                        Q-1      Q-1       H        CH.sub.3 CH.sub.3                                 Q-1      Q-2       H        CH.sub.3 OCH.sub.3                                Q-1      Q-3       H        OCH.sub.3                                                                              OCH.sub.3                                Q-1      Q-4       H        Cl.sup.b OCH.sub.3                                Q-1      Q-5       H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-1      Q-6       H        CH.sub.3 CH.sub.3                                 Q-1      Q-7       H        CH.sub.3 OCH.sub.3                                Q-1      Q-8       H        OCH.sub.3                                                                              OCH.sub.3                                Q-1      Q-9       H        Cl.sup.b OCH.sub.3                                Q-1      Q-10      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-1      Q-11      H        CH.sub.3 CH.sub.3                                 Q-1      Q-12      H        CH.sub.3 OCH.sub.3                                Q-1      Q-13      H        OCH.sub.3                                                                              OCH.sub.3                                Q-1      Q-14      H        Cl.sup.b OCH.sub.3                                Q-1      Q-15      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-1      Q-16      H        CH.sub.3 CH.sub.3                                 Q-1      Q-17      H        CH.sub.3 OCH.sub.3                                Q-1      Q-18      H        OCH.sub.3                                                                              OCH.sub.3                                Q-1      Q-19      H        Cl.sup.b OCH.sub.3                                Q-1      Q-20      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-2      Q-2       H        CH.sub.3 CH.sub.3                                 Q-2      Q-3       H        CH.sub.3 OCH.sub.3                                Q-2      Q-4       H        OCH.sub.3                                                                              OCH.sub.3                                Q-2      Q-5       H        Cl.sup.b OCH.sub.3                                Q-2      Q-6       H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-2      Q-7       H        CH.sub.3 CH.sub.3                                 Q-2      Q-8       H        CH.sub.3 OCH.sub.3                                Q-2      Q-9       H        OCH.sub.3                                                                              OCH.sub.3                                Q-2      Q-10      H        Cl.sup.b OCH.sub.3                                Q-2      Q-11      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-2      Q-12      H        CH.sub.3 CH.sub.3                                 Q-2      Q-13      H        CH.sub.3 OCH.sub.3                                Q-2      Q-14      H        OCH.sub.3                                                                              OCH.sub.3                                Q-2      Q-15      H        Cl.sup.b OCH.sub.3                                Q-2      Q-16      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-2      Q-17      H        CH.sub.3 CH.sub.3                                 Q-2      Q-18      H        CH.sub.3 OCH.sub.3                                Q-2      Q-19      H        OCH.sub.3                                                                              OCH.sub.3                                Q-2      Q-20      H        Cl.sup.b OCH.sub.3                                Q-3      Q-3       H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-3      Q-4       H        CH.sub.3 CH.sub.3                                 Q-3      Q-5       H        CH.sub.3 OCH.sub. 3                               Q-3      Q-6       H        OCH.sub.3                                                                              OCH.sub.3                                Q-3      Q-7       H        Cl.sup.b OCH.sub.3                                Q-3      Q-8       H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-3      Q-9       H        CH.sub.3 CH.sub.3                                 Q-3      Q-10      H        CH.sub.3 OCH.sub.3                                Q-3      Q-11      H        OCH.sub.3                                                                              OCH.sub.3                                Q-3      Q-12      H        Cl.sup.b OCH.sub.3                                Q-3      Q-13      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-3      Q-14      H        CH.sub.3 CH.sub.3                                 Q-3      Q-15      H        CH.sub.3 OCH.sub.3                                Q-3      Q-16      H        OCH.sub.3                                                                              OCH.sub.3                                Q-3      Q-17      H        Cl.sup.b OCH.sub.3                                Q-3      Q-18      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-3      Q-19      H        CH.sub.3 CH.sub.3                                 Q-3      Q-20      H        CH.sub.3 OCH.sub.3                                Q-4      Q-4       H        OCH.sub.3                                                                              OCH.sub.3                                Q-4      Q-5       H        Cl.sup.b OCH.sub.3                                Q-4      Q-6       H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-4      Q-7       H        CH.sub.3 CH.sub.3                                 Q-4      Q-8       H        CH.sub.3 OCH.sub.3                                Q-4      Q-9       H        OCH.sub.3                                                                              OCH.sub.3                                Q-4      Q-10      H        Cl.sup.b OCH.sub.3                                Q-4      Q-11      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-4      Q-12      H        CH.sub.3 CH.sub.3                                 Q-4      Q-13      H        CH.sub.3 OCH.sub.3                                Q-4      Q-14      H        OCH.sub.3                                                                              OCH.sub.3                                Q-4      Q-15      H        Cl.sup.b OCH.sub.3                                Q-4      Q-16      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-4      Q-17      H        CH.sub.3 CH.sub.3                                 Q-4      Q-18      H        CH.sub.3 OCH.sub.3                                Q-4      Q-19      H        OCH.sub.3                                                                              OCH.sub.3                                Q-4      Q-20      H        Cl.sup.b OCH.sub.3                                Q-5      Q-5       H        CH.sub.3 CH.sub.3                                 Q-5      Q-6       H        CH.sub.3 OCH.sub.3                                Q-5      Q-7       H        OCH.sub.3                                                                              OCH.sub.3                                Q-5      Q-8       H        Cl.sup.b OCH.sub.3                                Q-5      Q-9       H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-5      Q-10      H        CH.sub.3 CH.sub.3                                 Q-5      Q-11      H        CH.sub.3 OCH.sub.3                                Q-5      Q-12      H        CH.sub.3 OCH.sub.3                                Q-5      Q-13      H        OCH.sub.3                                                                              OCH.sub.3                                Q-5      Q-14      H        Cl.sup.b OCH.sub.3                                Q-5      Q-15      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-5      Q-16      H        CH.sub.3 CH.sub.3                                 Q-5      Q-17      H        CH.sub.3 OCH.sub.3                                Q-5      Q-18      H        OCH.sub.3                                                                              OCH.sub.3                                Q-5      Q-19      H        Cl.sup.b OCH.sub.3                                Q-5      Q-20      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-6      Q-6       H        CH.sub.3 CH.sub.3                                 Q-6      Q-7       H        CH.sub.3 OCH.sub.3                                Q-6      Q-8       H        OCH.sub.3                                                                              OCH.sub.3                                Q-6      Q-9       H        Cl.sup.b OCH.sub.3                                Q-6      Q-10      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-6      Q-11      H        CH.sub.3 CH.sub.3                                 Q-6      Q-12      H        CH.sub.3 OCH.sub.3                                Q-6      Q-13      H        OCH.sub. 3                                                                             OCH.sub.3                                Q-6      Q-14      H        Cl.sup.b OCH.sub.3                                Q-6      Q-15      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-6      Q-16      H        CH.sub.3 CH.sub.3                                 Q-6      Q-17      H        CH.sub.3 OCH.sub.3                                Q-6      Q-18      H        OCH.sub.3                                                                              OCH.sub.3                                Q-6      Q-19      H        Cl.sup.b OCH.sub.3                                Q-6      Q-20      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-7      Q-7       H        CH.sub.3 CH.sub.3                                 Q-7      Q-8       H        CH.sub.3 OCH.sub.3                                Q-7      Q-9       H        OCH.sub.3                                                                              OCH.sub.3                                Q-7      Q-10      H        Cl.sup.b OCH.sub.3                                Q-7      Q-11      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-7      Q-12      H        CH.sub.3 CH.sub.3                                 Q-7      Q-13      H        CH.sub.3 OCH.sub.3                                Q-7      Q-14      H        OCH.sub.3                                                                              OCH.sub.3                                Q-7      Q-15      H        Cl.sup.b OCH.sub.3                                Q-7      Q-16      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-7      Q-17      H        CH.sub.3 CH.sub.3                                 Q-7      Q-18      H        CH.sub.3 OCH.sub.3                                Q-7      Q-19      H        OCH.sub.3                                                                              OCH.sub.3                                Q-7      Q-20      H        Cl.sup.b OCH.sub.3                                Q-8      Q-8       H        CH.sub.3 CH.sub.3                                 Q-8      Q-9       H        CH.sub.3 OCH.sub.3                                Q-8      Q-10      H        OCH.sub.3                                                                              OCH.sub.3                                Q-8      Q-11      H        Cl.sup.b OCH.sub.3                                Q-8      Q-12      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-8      Q-13      H        CH.sub.3 CH.sub.3                                 Q-8      Q-14      H        CH.sub.3 OCH.sub.3                                Q-8      Q-15      H        OCH.sub.3                                                                              OCH.sub.3                                Q-8      Q-16      H        Cl.sup.b OCH.sub.3                                Q-8      Q-17      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-8      Q-18      H        CH.sub.3 CH.sub.3                                 Q-8      Q-19      H        CH.sub.3 OCH.sub.3                                Q-8      Q-20      H        OCH.sub.3                                                                              OCH.sub.3                                Q-9      Q-9       H        Cl.sup.b OCH.sub.3                                Q-9      Q-10      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-9      Q-11      H        CH.sub.3 CH.sub.3                                 Q-9      Q-12      H        CH.sub.3 OCH.sub.3                                Q-9      Q-13      H        OCH.sub.3                                                                              OCH.sub.3                                Q-9      Q-14      H        Cl.sup.b OCH.sub.3                                Q-9      Q-15      H        CH.sub.3 CH.sub.3                                 Q-9      Q-16      H        CH.sub.3 OCH.sub.3                                Q-9      Q-17      H        OCH.sub.3                                                                              OCH.sub.3                                Q-9      Q-18      H        Cl.sup.b OCH.sub.3                                Q-9      Q-19      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-9      Q-20      H        CH.sub.3 CH.sub.3                                 Q-10     Q-10      H        CH.sub.3 OCH.sub.3                                Q-10     Q-11      H        OCH.sub.3                                                                              OCH.sub.3                                Q-10     Q-12      H        Cl.sup.b OCH.sub.3                                Q-10     Q-13      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-10     Q-14      H        CH.sub.3 CH.sub.3                                 Q-10     Q-15      H        CH.sub.3 OCH.sub.3                                Q-10     Q-16      H        OCH.sub.3                                                                              OCH.sub.3                                Q-10     Q-17      H        Cl.sup.b OCH.sub.3                                Q-10     Q-18      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-10     Q-19      H        CH.sub.3 CH.sub.3                                 Q-10     Q-20      H        CH.sub.3 OCH.sub.3                                Q-11     Q-11      H        OCH.sub.3                                                                              OCH.sub.3                                Q-11     Q-12      H        Cl.sup.b OCH.sub.3                                Q-11     Q-13      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-11     Q-14      H        CH.sub.3 CH.sub.3                                 Q-11     Q-15      H        CH.sub.3 OCH.sub.3                                Q-11     Q-15      H        OCH.sub.3                                                                              OCH.sub.3                                Q-11     Q-16      H        Cl.sup.b OCH.sub.3                                Q-11     Q-17      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-11     Q-18      H        CH.sub.3 CH.sub.3                                 Q-11     Q-19      H        CH.sub.3 OCH.sub.3                                Q-11     Q-20      H        OCH.sub.3                                                                              OCH.sub.3                                Q-12     Q-12      H        Cl.sup.b OCH.sub.3                                Q-12     Q-13      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-12     Q-14      H        CH.sub.3 CH.sub.3                                 Q-12     Q-15      H        CH.sub.3 OCH.sub.3                                Q-12     Q-16      H        OCH.sub.3                                                                              OCH.sub.3                                Q-12     Q-17      H        Cl.sup.b OCH.sub.3                                Q-12     Q-18      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-12     Q-19      H        CH.sub.3 CH.sub.3                                 Q-12     Q-20      H        CH.sub.3 OCH.sub.3                                Q-13     Q-13      H        OCH.sub.3                                                                              OCH.sub.3                                Q-13     Q-14      H        Cl.sup.b OCH.sub.3                                Q-13     Q-15      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-13     Q-16      H        CH.sub.3 CH.sub.3                                 Q-13     Q-17      H        CH.sub.3 OCH.sub.3                                Q-13     Q-18      H        OCH.sub.3                                                                              OCH.sub.3                                Q-13     Q-19      H        Cl.sup.b OCH.sub.3                                Q-13     Q-20      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-14     Q-14      H        CH.sub.3 CH.sub.3                                 Q-14     Q-15      H        CH.sub.3 OCH.sub.3                                Q-14     Q-16      H        OCH.sub.3                                                                              OCH.sub.3                                Q-14     Q-17      H        Cl.sup.b OCH.sub.3                                Q-14     Q-18      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-14     Q-19      H        CH.sub.3 CH.sub.3                                 Q-14     Q-20      H        CH.sub.3 OCH.sub.3                                Q-15     Q-15      H        CH.sub.3 OCH.sub.3                                Q-15     Q-16      H        OCH.sub.3                                                                              OCH.sub.3                                Q-15     Q-17      H        Cl.sup.b OCH.sub.3                                Q-15     Q-18      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-15     Q-19      H        CH.sub.3 CH.sub.3                                 Q-15     Q-20      H        CH.sub.3 OCH.sub.3                                Q-16     Q-16      H        OCH.sub.3                                                                              OCH.sub.3                                Q-16     Q-17      H        Cl.sup.b OCH.sub.3                                Q-16     Q-18      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-16     Q-19      H        CH.sub.3 CH.sub.3                                 Q-16     Q-20      H        CH.sub.3 OCH.sub.3                                Q-17     Q-17      H        OCH.sub.3                                                                              OCH.sub.3                                Q-17     Q-18      H        Cl.sup.b OCH.sub.3                                Q-17     Q-19      H        OCF.sub.2 H                                                                            OCH.sub.3                                Q-17     Q-20      H        CH.sub.3 CH.sub.3                                 Q-18     Q-18      H        CH.sub.3 OCH.sub.3                                Q-18     Q-19      H        OCH.sub.3                                                                              OCH.sub.3                                Q-18     Q-20      H        Cl.sup.b OCH.sub.3                                Q-19     Q-19      H        CH.sub.3 CH.sub.3                                 Q-19     Q-20      H        CH.sub.3 OCH.sub.3                                Q-20     Q-20      H        OCH.sub.3                                                                              OCH.sub.3                                ______________________________________                                         .sup.a Z = N                                                                  .sup.b Z = CH                                                            

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid inertdiluent(s). More specifically, they will contain these ingredients inthe following approximate proportions:

                  TABLE 16                                                        ______________________________________                                                    Active  Weight Percent*                                                       Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions                                                          (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, mayd beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood. "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 10

Wettable Power

    ______________________________________                                        N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                        80%                                                 3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide                                  sodium alkylnaphthalene sulfonate                                                                       2%                                                  sodium ligninsulfonate    2%                                                  synthetic amorphous silica                                                                              3%                                                  kaolinite                 13%                                                 ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 11

Wettable Powder

    ______________________________________                                        N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                     50%                                               2,6-bis(methylthio)benzenesulfonamide                                         sodium alkylnaphthalenesulfonate                                                                           2%                                               low viscosity methyl cellulose                                                                             2%                                               diatomaceous earth          46%                                               ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 12

Granule

    ______________________________________                                        Wettable Powder of Example 11                                                                         5%                                                    attapulgite granules   95%                                                    (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 13 Extruded Pellet

    ______________________________________                                        N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                          25%                                               3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide                                  anhydrous sodium sulfate    10%                                               crude calcium ligninsulfonate                                                                              5%                                               sodium alkylnaphthalenesulfonate                                                                           1%                                               calcium/magnesium bentonite 59%                                               ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 14

Low Strength Granule

    ______________________________________                                        N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                     1%                                                2,6-bis(methylthio)benzenesulfonamide                                         N,N--dimethylformamide      9%                                                attapulgite granules        90%                                               (U.S.S. 20-40 sieve)                                                          ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 15

Aqueous Suspension

    ______________________________________                                        N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                     40%                                               2,6-bis(methylthio)benzenesulfonamide                                         polyacrylic acid thickener  0.3%                                              dodecylphenol polyethylene glycol ether                                                                   0.5%                                              disodium phosphate          1%                                                monosodium phosphate        0.5%                                              polyvinyl alcohol           1.0%                                              water                       56.7%                                             ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 16

Solution

    ______________________________________                                        N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                           5%                                               3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide,                                 sodium salt                                                                   water                       95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 17

Low Strength Granule

    ______________________________________                                        N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                      0.1%                                             2,6-bis(methylthio)benzenesulfonamide                                         attapulgite granules        99.9%                                             (U.S.S. 20-40 mesh)                                                           ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 18

Granule

    ______________________________________                                        N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                        80%                                                 3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide                                  wetting agent              1%                                                 crude ligninsulfonate salt (containing                                                                  10%                                                 5-20% of the natural sugars)                                                  attapulgite clay           9%                                                 ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 19

High Strength Concentrate

    ______________________________________                                        N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                      99%                                              2,6-bis(methylthio)benzenesulfonamide                                         silica aerogel               0.5%                                             synthetic amorphous silica   0.5%                                             ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 20

Wettable Powder

    ______________________________________                                        N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                          90%                                               3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide                                  dioctyl sodium sulfosuccinate                                                                             0.1%                                              synthetic fine silica       9.9%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 21

Wettable Powder

    ______________________________________                                        N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                    40%                                                2,6-bis(methylthio)benzenesulfonamide                                         sodium ligninsulfonate     20%                                                montmorillonite clay       40%                                                ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 22

Oil Suspension

    ______________________________________                                        N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                    35%                                                2,6-bis(methylthio)benzenesulfonamide                                         blend of polyalcohol carboxylic                                                                           6%                                                esters and oil soluble petroleum                                              sulfonates                                                                    xylene                     59%                                                ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 23

Dust

    ______________________________________                                        N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                        10%                                                 3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide                                  attapulgite               10%                                                 Pyrophyllite              80%                                                 ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

UTILITY

Test results indicate that the compounds of the present invention areactive herbicides. They should have utility for broad-spectrum preand/or postemergence weed control in areas where complete control of allvegetation is desired, such as around fuel storage tanks, ammunitiondepots, industrial storage areas, parking lots, drive-in theaters,around billboards, highway and railroad structures. Alternatively, manyof the subject compounds should be useful for the selective pre orpostemergence weed control in crops, especially wheat and sugar beets.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as selective orgeneral herbicides, the crop species involved, the types of weeds to becontrolled, weather and climate, formulations selected, mode ofapplication, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.005 to 10kg/ha, the lower rates being suggested for use on lighter soils and/orthose having a low organic matter content, or for situations where onlyshort-term persistence is required.

The compounds of the invention may be used in combination with any othercommercial herbicide, examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

Test A

Seeds of crabgrass (Digitaria sp.), barnyard-grass (Echinochloacrusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia),morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn,soybean, sugar beet, rice, wheat and purple nutsedge (Cyperus rotundus)tubers were planted and treated preemergence with the test chemicalsdissolved in a non-phytotoxic solvent. At the same time, these crop andweed species, along with cotton and bush bean, were treated with asoil/foliage application. At the time of treatment, the plants ranged inheight from 2 to 18 cm. Treated plants and controls were maintained in agreenhouse for sixteen days, after which all species were compared tocontrols and visually rated for response to treatment. The ratings,summarized in Table A, are based on a numerical scale extending from0=no injury, to 10=complete kill. The accompanying descriptive symbolshave the following meanings:

C=chlorosis/necrosis;

E=emergence inhibition;

G=growth retardation;

H=formative effects;

U=unusual pigmentation; and

6Y=abscised buds or flowers. ##STR120##

                                      TABLE A                                     __________________________________________________________________________            Cmpd. 1                                                                            Compound 2  Cmpd. 3                                                                             Cmpd. 4                                                                             Cmpd. 5                                                                             Cmpd. 6                                                                             Cmpd. 7                      Rate g/ha                                                                             50   50    400   50    50    50    50    50                           __________________________________________________________________________    POSTEMERGENCE                                                                 Bush bean                                                                             3C,3H                                                                              5C,9G,6Y                                                                            6C,9G,6Y                                                                            4C,8H,6Y                                                                            4C,9G,6Y                                                                            2C,7G,6Y                                                                            4C,8H,6Y                                                                            3C,8G,6Y                     Cotton  4C,8G                                                                              4C,9G 4C,9G 4C,9G 5C,9G 4C,9G 5C,9H 2C,2H,5G                     Morningglory                                                                          9C   4C,9G 5C,9G 5C,9G 5C,9G 4C,9G 4C,7G 2C                           Cocklebur                                                                             9C   9C    9C    5C,9G 9C    9C    9C    3C,8H                        Sicklepod                                                                             4C,3H                                                                              2C,2H 2C,6G 4C,9G 9C    5C,9G 5C,9G 2C,5G                        Nutsedge                                                                              4C,9G                                                                              8G    4C,9G 4C,9G 9C    2C,9G 5C,9G 1C,5G                        Crabgrass                                                                             4G   2C,5G 2C,8G 2C,5G 2C,9G 2C,8G 2C,8G 5G                           Barnyardgrass                                                                         4C,9H                                                                              2C,7H 5C,9G 3C,9H 9C    9C    9C    3C,9H                        Wild Oats                                                                             3C,5G                                                                              2C,4G 4C,9G 2C    9C    9C    5C,9G 5G,2C                        Wheat   5G   3G    9G    3G    9C    10C   9C    1C,3G                        Corn    2C,6H                                                                              2C,9H 1U,9G 2C,8H 9C    3U,9G 2C,9H 2C,9H                        Soybean 5C,9G                                                                              5C,9G 5C,9G 5C,9G 4C,9G 5C,9G 5C,9G 3C,7G                        Rice    2C,7G                                                                              2C,4G 2C,8G 1C,1H 5C,9G 5C,9G 5C,9G 4C,9G                        Sorghum 3C,8H                                                                              3C,9G 5C,9G 2C,9G 5U,9G 5C,9G 4C,9G 3C,9G                        Sugar beet                                                                            2C,8G                                                                              2C    4C,8G 2C,8G 9C    9C    9C    2C,8G                        PREEMERGENCE                                                                  Morningglory                                                                          2C,9G                                                                              2C,8H 9C    4C,9G 9C    9C    9G    8G                           Cocklebur                                                                             9H   9H    9H    9H    9H    9H    9H    --                           Sicklepod                                                                             3C,6G                                                                              2C,2G 2C,9G 4C,5H 9C    4C,9G 9G    9G                           Nutsedge                                                                              2C,6G                                                                              5G    10E   4C,6G 10E   10E   10E   0                            Crabgrass                                                                             2G   2G    7G    2G    4C,9G 3C,5G 1C    2G                           Barnyardgrass                                                                         5C,6G                                                                              3C,7G 5C,9H 5C,6G 5C,9H 5C,9H 5C,9H 2C,8H                        Wild Oats                                                                             2C,8G                                                                              3C,8G 5C,9H 3C    5C,9G 5C,9H 5C,9G 2C,8G                        Wheat   8G   2C,8G 3C,9H 1C,4G 10C   10H   4C,9H 7G                           Corn    2C,8H                                                                              2C,9H 4C,9H 9G    10E   9H    3C,9H 2C,8G                        Soybean 4C,5G                                                                              4C,6H 9H    5C,6H 9H    8H    9H    1C,3G                        Rice    4C,6G                                                                              4C,6G 4C,9H 3C,3G 10E   10E   10E   2C,9H                        Sorghum 4C,9H                                                                              3C,9H 10H   5C,9G 5C,9H 10H   5C,9H 5C,9H                        Sugar beet                                                                            3C,9G                                                                              2C,9G 9G    8G    10C   9C    5C,9G 5C,9G                        __________________________________________________________________________            Cmpd. 8                                                                             Cmpd. 9                                                                             Cmpd. 10                                                                            Cmpd. 11                                                                            Cmpd. 12                                                                            Cmpd. 13                                                                            Cmpd. 14                                                                            Cmpd. 15                    Rate g/ha                                                                             50    50    50    50    50    50    50    50                          __________________________________________________________________________    POSTEMERGENCE                                                                 Bush bean                                                                             5C,9G,6Y                                                                            2H                                                              Cotton  4C,9G 2C    5C,9G 5C,9G 2C,8H 2C,8G 2C,8G 2C,8G                       Morningglory                                                                          2C,4G 1C    10C   10C   3C,9G 3C,8G 2C,5G 4C,9G                       Cocklebur                                                                             3C,9H 2C,5G 9C    9C    3C,9G 3C,9G 2C,7H 5C,9G                       SicklePod                                                                             4C,9G 5G    4C,8G 4C,7G 3C    2C    2C,3G 3C,6H                       Nutsedge                                                                              4G    2G    6C,9G 4C,9G 2C,8G 3C,9G 10C   3C,9G                       Crabgrass                                                                             2C,5G 5G    5C,8G 0     2G    0     3H    0                           Barnyardgrass                                                                         2C,8H 2C,3G 10C   9C    3C,8H 3C,8H 2C,8H 9C                          Wild Oats                                                                             2C,8H 0     9C    9C    5G    0     0     9C                          Wheat   6C,9G 0     9C    3C,9G 0     2G    0     9C                          Corn    4C,9H 2C,3G 3C,9G 2U,9G 0     0     1H    3H                          Soybean 3C,9G 2C,5G 3C,9G 4C,9G 2C,9G 2C,9G 2C,9G 3C,9G                       Rice    5C,9G 2C    3G    4C,9G 5G    4G    5G    2C,9G                       Sorghum 2C,9G 9H    10C   9C    2C,8G 2C,9G 2C,8H 3C,9G                       Sugar beet                                                                            3C,9G 2C,8G 10C   10C   5G    5G    3G    3C,9G                       PREEMERGENCE                                                                  Morningglory                                                                          8G    7G    9G    9H    2C,7H 9C    9G    9C                          Cocklebur                                                                             9H    8H    9H    9H    9H    9H    9H    9H                          Sicklepod                                                                             7G    6G    5C,8G 6G,5C 2C,7G 8G    7G    3C,7G                       Nutsedge                                                                              10E   10E   2C,5G 0     5G    2C,9G 5G    0                           Crabgrass                                                                             0     2G    1C    0     0     0     0     0                           Barnyardgrass                                                                         2C,5G 2C,7G 1C    2C    2C,6H 3C,8H 2C,7G 4G                          Wild Oats                                                                             2C,7G 2C,7G 3C,9G 5C,9G 2C,9G 2C,8G 2C    2C,8G                       Wheat   2C,7G 9G    2C,4G 8G    2G    2C,7G 3G    3G                          Corn    2C,7G 2C,5G 3C,9G 9G    5G    2C,8G 2C,7H 2C,9H                       Soybean 1C,1H 1C,1H 3C,7H 3C,8H 2C,3H 3C,7H 1C,1H 3C,5H                       Rice    3C,9H 3C,9H 3C,4G 5G    2C,6G 2C,6G 3C,6G 7G                          Sorghum 2C,9H 5C,9H 5C,9H 6C,9H 2C,9H 2C,9H 3C,7H 2C,9G                       Sugar beet                                                                            3C,9G 3C,9G 9C    10C   8G    2C,9G 7G    9G                          __________________________________________________________________________

To better define the utility of the compounds of this invention, severalof the compounds were tested in Tests B-F.

Test B

Two plastic bulb pans were filled with fertilized and limed Woodstownsandy loam soil. One pan was planted with corn, sorghum, Kentuckybluegrass and several grass weeds. The other pan was planted withcotton, soybeans, rapeseed, purple nutsedge (Cyperus rotundus), andseveral broadleaf weeds. The following grass and broadleaf weeds wereplanted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense),dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii),cheatgrass (Bromus secalinus), cocklebur (Xanthium pensylvanicum),morningglory (Ipomoea hederacea), sicklepod (Cassia obtusifolia),teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), andjimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was alsofilled with prepared soil and planted with rice and wheat. Another 12.5cm pot was planted with sugar beets. The above four containers weretreated preemergence with several test compounds within the scope of theinvention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. Compounds 1-6 eachexhibited a broad-spectrum of control at application rates as low as 16g/ha; Compounds 1, 2 and 3 were also safe on wheat at application ratesas high as 125 g/ha. Compounds 7-9 showed some activity at 16 g/ha, butexhibited a broader spectrum of activity at rates of 62 g/ha and above.Compounds 7 and 8 also showed some safety on wheat. The data for severalof the compounds tested are summarized in Table B.

                                      TABLE B                                     __________________________________________________________________________    PREEMERGENCE ON                                                               WOODSTOWN SANDY LOAM                                                                  Compound 1                                                                           Compound 2                                                                           Compound 5                                                                            Compound 7                                      Rate g/ha                                                                             16 125 16 125 8   62  4 16                                                                              62                                                                              250                                       __________________________________________________________________________    Crabgrass                                                                             0  0   0  2G  2G  7G  0 0 0 0                                         Barnyardgrass                                                                         3G 9G  2G 9G  5G  9G  0 0 0 7G                                        Sorghum 9G 9G  7G 9G  9G  9G  --                                                                              --                                                                              --                                                                              --                                        Wild Oats                                                                             2G 8G  2G 7G  6G  9G  0 0 0 5G                                        Johnsongrass                                                                          3G 9G  5G 9G  8G  9G  0 0 0 7G                                        Dallisgrass                                                                           0  6G  3G 3G  3G  8G  --                                                                              --                                                                              --                                                                              --                                        Giant foxtail                                                                         3G 4G  4G 3G  3G  8G  0 0 0 2G                                        Ky. bluegrass                                                                         -- --  -- --  3G  9G  --                                                                              --                                                                              --                                                                              --                                        Cheatgrass                                                                            6G 8G  7G 9G  9G  10C --                                                                              --                                                                              --                                                                              --                                        Sugar beets                                                                           5G 10C 5G 8G  6G  9G  0 3G                                                                              7G                                                                              9G                                        Corn    2G 5G,3C                                                                             3G 9G  3G,2C                                                                             4G,2C                                                                             0 0 4G                                                                              8G                                        Rape    9G 10C 9G 9G  5G  9G  --                                                                              --                                                                              --                                                                              --                                        Cocklebur                                                                             6G 9G  7G 9G  5G  9G  0 0 7G                                                                              9G                                        Nutsedge                                                                              7G 10C 4G 10C 3G  8G  0 0 3G                                                                              8G                                        Cotton  9G 8G  8G 6G  5G  7G  0 0 3G                                                                              7G                                        Morningglory                                                                          6G 9G  3G 7G  0   8G  0 0 0 5G                                        Sicklepod                                                                             5G 7G  2G 6G  0   8G  0 0 4G                                                                              9G                                        Teaweed 5G 8G  2G 6G  3G  8G  0 0 3G                                                                              7G                                        Velvetleaf                                                                            5G 8G  0  8G  5G  8G  0 0 2G                                                                              9G                                        Jimsonweed                                                                            3G 9G  0  8G  7G  9G  0 0 3G                                                                              2G                                        Soybean 2G 8G,7H                                                                             0  6G,3H                                                                             3G  8G,7H                                                                             0 0 2G                                                                              7G                                        Rice    8G 9G  7G 3G  8G  10C 0 3G                                                                              8G                                                                              10G                                       Wheat   0  2G  0  0   2G  7G  0 0 0 5G                                        __________________________________________________________________________

Test C

The test chemicals, dissolved in a non-phytotoxic solvent, were appliedin an overall spray to the foliage and surrounding soil of selectedplant species. Approximately fourteen days after treatment, all specieswere visually compared to untreated controls and rated for response totreatment. The rating system was as described previously for Test A. Thedata are presented in Table C.

All plant species were seeded in Woodstown sandy loam soil and grown ina greenhouse. The following species were grown in soil contained inplastic pots (25 cm diameter by 13 cm deep): soybeans, cotton, alfalfa,corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania(Sesbania exaltata), Sicklepod (Cassia obtusifolia), morningglory(Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthiumpensylvanicum), crabgrass (Digitaria sp.), nutsedge (Cyperus rotundus),barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii)and wild oats (Avena fatua). The following species were grown in soil ina paper cup (12 cm diameter by 13 cm deep): sunflower, sugar beets, andmustard. All plants were sprayed approximately 14 days after planting.Additional plant species such as johnson-grass and field bindweed aresometimes added to this standard test.

Compounds 1-5 were tested by this procedure, and each exhibitedpostemergence activity at application rates as low as 4 g/ha. Compounds2 and 3 were safe on wheat, and Compound 3 was also safe on sugar beets.Data for these compounds are presented in Table C.

                                      TABLE C                                     __________________________________________________________________________    Over-the-Top Soil/Foliage Treatment                                                   Cmpd. 1                                                                            Cmpd. 2                                                                            Cmpd. 3                                                                            Compound 4   Compound 5                                Rate g/ha                                                                             4 16 4 16 4 16 1 4  16  62  4   16  62                                __________________________________________________________________________    Soybeans                                                                              7G                                                                              8G 3C                                                                              8C 8C                                                                              9C 8G                                                                              10C                                                                              10C 10C 7G  10C 10C                               Velvetleaf                                                                            3G                                                                              6G 5G                                                                              7G 4G                                                                              6G 2C                                                                              6C 7C,7G                                                                             7C,8G                                                                             5C,5G                                                                             7C,7G                                                                             6C,7G                             Sesbania                                                                              5G                                                                              8G 4G                                                                              7G 8G                                                                              8G --                                                                              4G 9G  9C  8G  9G  9G                                Sicklepod                                                                             0 5G 0 0  2C                                                                              6C 2C                                                                              0  9G  9G  4G  8G  9G                                Cotton  0 5G 5G                                                                              6G 4G                                                                              5G 5G                                                                              4C 9G  10C 7G  9G  10C                               Morningglory                                                                          7G                                                                              9G 6G                                                                              8G 2G                                                                              8G 5G                                                                              8G 8C,8G                                                                             9G  7G  8G  10C                               Bush Bean                                                                             --                                                                              -- --                                                                              -- --                                                                              -- --                                                                              -- 7C,7G                                                                             8C,8G                                                                             4G,4C                                                                             10C 10C                               Jimsonweed                                                                            8G                                                                              9G 5G                                                                              5G 0 -- 0 0  9G  9G  5G  7G  8G                                Cocklebur                                                                             3G                                                                              8G 6G                                                                              8G 7G                                                                              7G 2G                                                                              -- 8G  9G  8G  8G  9G                                Sunflower                                                                             --                                                                              -- --                                                                              -- --                                                                              -- --                                                                              -- 9C  10C 5G  8G  10C                               Mustard --                                                                              -- --                                                                              -- --                                                                              -- --                                                                              -- 8G  9G  7G  10C 10C                               Sugar beets                                                                           6G                                                                              6G 2G                                                                              6G 0 0  3G                                                                              7G 9G  10C 8G  10C 10C                               Corn    0 2G 2G                                                                              4G 0 4H 3G                                                                              5G 7G  7G  1G  6G  6G,6C                             Crabgrass                                                                             0 0  0 0  0 0  0 0  8G  8G  0   1G  3G                                Rice    0 0  0 0  2G                                                                              0  1C                                                                              5C 7G  7G  2G  7G,4C                                                                             5C,7G                             Nutsedge                                                                              0 0  0 0  2C                                                                              8G 2G                                                                              3G 6G  8C  1G  5G  8G                                Barnyardgrass                                                                         0 7G 2G                                                                              0  4G                                                                              5G 2G                                                                              9G 8G  9C  7G  8G  8G,6C                             Wheat   0 3G 0 0  0 0  0 5G 6G  8G  4G  4G  5G                                Giant foxtail                                                                         0 2G 0 0  0 0  0 4G 7G  9G  2G  5G  8G                                Wild Oats                                                                             0 2G 0 0  0 0  0 4G 7G  8G  5G  7G  7G                                Sorghum --                                                                              -- --                                                                              -- --                                                                              -- 0 5G 8G  9C  8G  9G  9G                                Johnsongrass                                                                          0 3G 1G                                                                              3G 4G                                                                              7G 3G                                                                              9C 10C 10C 4G  7G  7C,8G                             Field Bindweed                                                                        --                                                                              -- --                                                                              -- --                                                                              -- 0 6C 3G  5G  1G  0   0                                 __________________________________________________________________________

Test D

Two plastic pans lined with polyethylene liners were filled withprepared Woodstown sandy loam soil. One pan was planted with seeds ofwheat (Triticum aestivum), barley (Hordeum vulgare), wild oats (Avenafatua), cheatgrass (Bromus secalinus), blackgrass (Alopecurusmyosuroides), annual bluegrass (Poa annua), green foxtail (Setariaviridis), Italian ryegrass (Lolium multiflorum) and rapeseed (Brassicanapus). The other pan was planted with seeds of Russian thistle (Salsolakali), cleavers (Galium aparine), speedwell (Veronica persica), kochia(Kochia scoparia), shepherdspurse (Capsella bursa-pastoris), Matricariainodora, black nightshade (Solanum nigrum), wild buckwheat (Polygonumconvolvulus) and sugar beets (Beta vulgaris). The above two pans weretreated preemergence. At the same time two pans in which the above plantspecies were growing were treated postemergence. Plant heights at thetime of treatment ranged from 1-20 cm depending on plant species.

The compounds applied were diluted with a non-phytotoxic solvent andsprayed over-the-top of the pans. An untreated control and a solventalone control were included for comparison. All treatments weremaintained in the greenhouse for 19-22 days at which time the treatmentswere compared to the controls and the effects visually rated. Therecorded data are presented in Table D. Each of the tested compoundsprovides control of certain weeds at rates of application which causeno, or minimum injury to sugar beets.

                                      TABLE D                                     __________________________________________________________________________             Compound 1      Compound 2      Compound 3                                    Preemergence                                                                          Postemergence                                                                         Preemergence                                                                          Postemergence                                                                         Preemergence                                                                          Postemergence                Rate g/ha                                                                              15  60  15  60  15  60  15  60  15  60  15  60                       __________________________________________________________________________    wheat    0   2G  0   0   0   0   0   2G  1G  2G,1C                                                                             0   0                        barley   2G  7G  0   0   0   3G  0   3G  1G  1C  0   1G                       wild oats                                                                              3G  6G  0   1G  0   4G  0   3G  1G,2C                                                                             3G  0   0                        cheatgrass                                                                             3G  6G  0   1G  1C  1G,4C                                                                             0   2G  0   0   0   0                        blackgrass                                                                             9G  9G  0   1G  0   4G  0   3G  6G  7G  0   3G                       annual bluegrass                                                                       4G  7G  0   0   0   0   0   1G  2G  2G  0   2G                       green foxtail                                                                          2G  3G  0   0   0   0   0   0   0   3G  0   0                        Italian ryegrass                                                                       2G  3G  0   0   0   0   0   0   2G  5G  0   0                        rapeseed 7G  8G  3G  8G  1C  10C 10C 8G,1C                                                                             8G  10C 9G,9C                                                                             10C                      Matricaria inodora                                                                     6G  9G  6G,2C                                                                             8G,3C                                                                             8G  8G  3G  6G,4C                                                                             9G  9G  5G,2C                                                                             9G,7C                    Galium aparine                                                                         10C 10C 10C 10C 10C 10C --  10C --  10C --  10C                      Russian thistle                                                                        4G  10C 0   0   0   0   0   1G  0   0   5G  7G                       shepherdspurse                                                                         4G  10C 7G  9G  8G  10C 7G  9G  10C 10C 10C 10C                      kochia   0   0   0   0   0   6G  0   4G  2G  2G  0   1G                       black nightshade                                                                       2G  8G,3C                                                                             6G  8G,7C                                                                             7G  9G,9C                                                                             3G,2C                                                                             8G,8C                                                                             3G  4G  3G,4C                                                                             7G,3C                    speedwell                                                                              0   6G  2G  8G  6G  8G,3C                                                                             2C,4G                                                                             8G,7C                                                                             2G  7G  8G,7C                                                                             9G,2C                    wild buckwheat                                                                         0   6G  2G,1C                                                                             8G,8C                                                                             0   5G  2C  7G,4C                                                                             5G  6G  9G,5C                                                                             8G,3C                    sugar beets                                                                            0   0   0   0   0   6G  0   0   0   2G,1C                                                                             0   0                        __________________________________________________________________________

Test E

Compounds 2 and 3 were further evaluated for their utility as selectivesugar beet herbicides in a test which differed from Test D only in thetypes of certain weed species. The compounds were applied both pre andpostemergence to the species shown in Table E. The relative tolerance ofsugar beets is again evident from the data presented in Table E.

                                      TABLE E                                     __________________________________________________________________________             Compound 2  Compound 3                                                                            Compound 2  Compound 3                                    PreEmergence        PostEmergence                                    Rate g/ha                                                                              4   15  60  30  125 4   15  60  30  125                              __________________________________________________________________________    wheat    0   1G  2G  0   2G  0   0   4G  0   0                                barley   0   1G  2G  0   4G  0   0   4G  0   2G                               wild oats                                                                              0   1G  2G  0   0   0   0   3G  0   0                                ryegrass 0   2G  1G  0   2G  0   0   2G,4C                                                                             0   1G                               annual bluegrass                                                                       0   0   4G  0   3G  0   0   5G  0   0                                blackgrass                                                                             0   0   5G  0   1G  0   0   5G  0   0                                green foxtail                                                                          0   0   0   0   0   0   1G  2G  0   0                                Matricaria inodora                                                                     9G  8G  9G  9G,7C                                                                             9G,7C                                                                             0   2C  2G,4C                                                                             8G,8C                                                                             9G,9C                            Galium aparine                                                                         0   4G,3C                                                                             10C 0   0   1C  4C  5G,5C                                                                             7G  10C                              kochia   0   3G  8G  0   1C  0   0   0   3G  2G                               black nightshade                                                                       8G  9G  9G,7C                                                                             2G,1C                                                                             7G  6G,2C                                                                             5G,4C                                                                             9G,4C                                                                             6G  8G,7C                            speedwell                                                                              0   2C  8G,8C                                                                             6G,5C                                                                             8G  0   0   4G,5C                                                                             8G  9G,4C                            wild buckwheat                                                                         2G  4G,3C                                                                             8G,8C                                                                             4G,2C                                                                             8G,3C                                                                             0   1C  2G,3C                                                                             0   7G,5C                            wild mustard                                                                           7G,1C                                                                             9G,9C                                                                             9G,9C                                                                             7G,2C                                                                             9G,9C                                                                             4C  7G,6C                                                                             8G,7C                                                                             9G,7C                                                                             10C                              wild radish                                                                            1G,1C                                                                             9G  10C 7G,4C                                                                             9G,9C                                                                             5G,2C                                                                             7G,6C                                                                             10C 10C 10C                              sugar beets                                                                            3G  7G  8G  2G,1C                                                                             8G  0   3G  3G,2C                                                                             0   2G,3C                            __________________________________________________________________________

Test F

Postemergence

Two round pans (25 cm diameter by 12.5 cm deep) were filled withSassafras sandy loam soil. One pan was planted with blackgrass(Alopecurus myosuroides), sugarbeets, nutsedge (Cyperus rotundus)tubers, crabgrass (Digitaria sanguinalis), sicklepod (Cassiaobtusifolia), teaweed (Sida spinosa), jimsonweed (Datura stramonium),velvetleaf (Abutilon theophrasti), and giant foxtail (Setaria faberii).The other pan was planted with wheat, cotton, rice, corn, soybean, wildoats (Avena fatua), cocklebur (Xanthium pensylvanicum), morningglory(Ipomoea hederacea), johnsongrass (Sorghum halepense) and barnyardgrass(Echinochloa crusgalli). The plants were grown for approximatelyfourteen days, then sprayed postemergence with the chemicals dissolvedin a non-phytotoxic solvent.

Preemergence

Two round pans (25 cm diameter by 12.5 cm deep) were filled withSassafras sandy loam soil. One pan was planted with blackgrass(Alopecurus myosuroides), sugarbeets, nutsedge, crabgrass, sicklepod,teaweed, jimsonweed, velvetleaf, and giant foxtail. The other pan wasplanted with wheat, cotton, rice, corn, soybeans, wild oats, cocklebur,morningglory, johnsongrass, and barnyardgrass. The two pans were sprayedpreemergence with the chemicals dissolved in a non-phytotoxic solvent.

Treated plants and controls were maintained in the greenhouse for 28days, then all treated plants were compared to controls and visuallyrated for plant response utilizing the rating system peviously describedfor Test A.

Response ratings are contained in Table F.

                                      TABLE F                                     __________________________________________________________________________           Compound 10         Compound 11         Compound 12                           Postemergence                                                                           Preemergence                                                                            Postemergence                                                                           Preemergence                                                                            Postemergence                                                                         Preemergence           Rate g/ha                                                                            1 4 16 62 4 16                                                                              62 250                                                                              1 4  16                                                                              62 4 16                                                                              62 250                                                                              4  16                                                                              62 16 62                                                                              250               __________________________________________________________________________    corn   0 3G                                                                              8G 9G 0 0 2G 8G 0 2G 8G                                                                              10G                                                                              0 0 2G 7G 0  0         0                                                                             0                                                                             0                                                                             0                 wheat  0 0 0  0  0 0 2G 8G 0 0  3G                                                                              6G 0 2G                                                                              5G 9G 0  0         0                                                                             0                                                                             0                                                                             0                 rice   0 0 0  2G 0 2G                                                                              5G 10B                                                                              0 0  2G                                                                              3C 0 2G                                                                              9G 9G 0  0         0                                                                             0                                                                             4G                                                                            8G                soybean                                                                              4G                                                                              7G                                                                              9G 9G 2C                                                                              4H                                                                              8G 9G 3G                                                                              6G 9G                                                                              10G                                                                              0 2C                                                                              5G 8G 2G 7G        10G                                                                           0                                                                             2G                                                                            5G                cotton 0 2C                                                                              7G 8G 0 0 2G 6C 0 2G 8G                                                                              9G 0 0 0  2C 0  0         3G                                                                            0                                                                             0                                                                             4G                sugarbeet                                                                            0 5G                                                                              10C                                                                              10C                                                                              2G                                                                              5G                                                                              10E                                                                              10B                                                                              0 5G 9G                                                                              10G                                                                              5G                                                                              7G                                                                              10B                                                                              10E                                                                              0  4G        8G                                                                            0                                                                             0                                                                             4G                crabgrass                                                                            0 0 0  3G 0 0 2G 9G 0 0  3G                                                                              5G 0 2G                                                                              4G 7G 0  0         0                                                                             0                                                                             0                                                                             0                 johnsongrass                                                                         0 3G                                                                              8G 10G                                                                              2G                                                                              4G                                                                              8G 9B 0 3G 8C                                                                              10C                                                                              2G                                                                              4G                                                                              6C 9G 0  0         0                                                                             0                                                                             3G                                                                            9G                blackgrass                                                                           0 0 5G 9G 2G                                                                              4G                                                                              8E 10E                                                                              0 4G 8G                                                                              10C                                                                              2G                                                                              4G                                                                              8E 10E                                                                              0  0         3G                                                                            3G                                                                            5G                                                                            8G                barnyardgrass                                                                        0 4G                                                                              7G 10C                                                                              0 2C                                                                              7G 9G 0 4G 6G                                                                              10C                                                                              0 0 5G 8G 0  0         0                                                                             0                                                                             2G                                                                            6G                nutsedge                                                                             0 0 3G 8G 0 3G                                                                              7G 10E                                                                              0 0  5G                                                                              9C 0 2G                                                                              4G 9G 0  3G        6G                                                                            0                                                                             2G                                                                            6G                giant foxtail                                                                        0 0 2G 4G 0 0 6G 10E                                                                              0 0  0 5G 0 0 6G 7G 0  0         0                                                                             0                                                                             2G                                                                            8G                wild oats                                                                            0 0 3G 5C 0 0 3G 9G 0 0  4G                                                                              9C 0 2G                                                                              5G 8G 0  0         0                                                                             0                                                                             0                                                                             0                 cocklebur                                                                            3G                                                                              9G                                                                              9G 9G 2G                                                                              6G                                                                              9G 9G 3G                                                                              5G 8G                                                                              9G 0 3G                                                                              7G 9G 4G 9G        10G                                                                           0                                                                             5G                                                                            9G                morningglory                                                                         2G                                                                              6G                                                                              7G 9G 0 2C                                                                              6G 9G 0 3G 8G                                                                              9G 0 2C                                                                              4H 8H 3G 8G        10G                                                                           0                                                                             0                                                                             6G                teaweed                                                                              0 0 0  2G 0 0 2C 8G 0 0  0 3G 0 0 3C 5C 0  0         0                                                                             0                                                                             0                                                                             5G                sicklepod                                                                            0 0 3G 3G 0 0 2C 7G 0 0  2G                                                                              5G 0 0 4G 5G 0  2G        4G                                                                            0                                                                             0                                                                             5G                jimsonweed                                                                           0 4G                                                                              8G 10G                                                                              0 0 3G 8G 0 0  3G                                                                              9G 0 0 4G 8C 2G 6G        9G                                                                            0                                                                             3G                                                                            8G                velvetleaf                                                                           0 3G                                                                              6G 5G 0 2C                                                                              5C 9G 0 0  3G                                                                              10C                                                                              0 0 2C 6G 0  0         5G                                                                            0                                                                             2G                                                                            8G                __________________________________________________________________________           Compound 13      Compound 14        Compound 15                               Postemergence                                                                          Preemergence                                                                          Postemergence                                                                            Preemergence                                                                          Postemergence                                                                            Preemergence            Rate g/ha                                                                            4 16                                                                              62                                                                              250                                                                              16 62                                                                              250                                                                              4 16 62 250                                                                              62  250 4 16 62 250                                                                              16 62 250               __________________________________________________________________________    corn   0 0 2G                                                                              6G 0  0 2G 0 0  0  0  0   5G  0 0  3G 6G 0      4G                                                                     9G                      wheat  0 0 0 0  0  0 2G 0 0  0  0  0   0   0 0  0  4G 0      5G                                                                     7G                      rice   0 0 0 2G 0  2G                                                                              6G 0 0  0  0  3G  7G  0 0  4G 10G                                                                              3G     9G                                                                     10G                     soybean                                                                              2G                                                                              5G                                                                              8G                                                                              9G 0  3G                                                                              6G 2G                                                                              7G 9G 9G 0   6G  2G                                                                              6G 9G 10G                                                                              3G     7G                                                                     9G                      cotton 0 0 3G                                                                              8G 0  0 3G 0 0  4G 8G 0   0   0 2G 7G 10G                                                                              0      2G                                                                     7G                      sugarbeet                                                                            0 0 4G                                                                              9G 0  5G                                                                              7G 0 0  3G 10C                                                                              0   2G  3G                                                                              10C                                                                              10C                                                                              10C                                                                              2G     8G                                                                     10G                     crabgrass                                                                            0 0 0 0  0  0 0  0 0  0  0  0   0   0 0  0  0  0      3G                                                                     6G                      johnsongrass                                                                         0 0 0 3G 0  3G                                                                              7G 0 0  0  0  0   0   0 3G 10C                                                                              10C                                                                              3G     9G                                                                     10G                     blackgrass                                                                           0 0 3G                                                                              8G 3G 7G                                                                              9G 0 5G 9C 9C 5G  10G 0 5G 10G                                                                              10G                                                                              3G     7G                                                                     10G                     barnyardgrass                                                                        0 0 2G                                                                              7G 0  7G                                                                              10G                                                                              0 0  0  6G 4G  9G  0 4G 10G                                                                              10C                                                                              3G     8G                                                                     10G                     nutsedge                                                                             0 4G                                                                              7G                                                                              9G 0  0 2G 4G                                                                              9C 10C                                                                              10C                                                                              4G  9G  3G                                                                              7C 10C                                                                              10C                                                                              0      4G                                                                     10E                     giant foxtail                                                                        0 0 0 2G 0  4G                                                                              8G 0 0  0  0  3G  7G  0 2G 6G 10G                                                                              2G     10G                                                                    10E                     wild oats                                                                            0 0 0 0  0  2G                                                                              5G 0 0  0  0  0   0   0 3G 7C 9C 0      5G                                                                     8G                      cocklebur                                                                            3G                                                                              9G                                                                              9G                                                                              10G                                                                              3G 8G                                                                              9G 0 5G 7G 10G                                                                              2C  9G  8G                                                                              9G 10G                                                                              10C                                                                              2G     8G                                                                     9G                      morningglory                                                                         0 3G                                                                              6G                                                                              10G                                                                              0  0 3G 0 5G 8G 10G                                                                              0   0   3G                                                                              8G 10G                                                                              10G                                                                              0      4G                                                                     7C                      teaweed                                                                              0 0 0 3G 0  3G                                                                              7G 0 0  0  3G 0   0   0 0  0  3G 0      4G                                                                     5G                      sicklepod                                                                            0 0 0 3G 0  0 6G 0 0  0  3G 0   0   0 5G 7G 10C                                                                              0      5G                                                                     7G                      jimsonweed                                                                           0 0 4G                                                                              10G                                                                              4G 8G                                                                              9G 0 3G 7G 10G                                                                              3G  8G  4G                                                                              9G 10G                                                                              10G                                                                              0      3G                                                                     9G                      velvetleaf                                                                           0 2G                                                                              7G                                                                              9G 2G 7G                                                                              8G 0 4G 7G 10G                                                                              2G  8G  0 7C 9G 10C                                                                              0      4G                                                                     9G                      __________________________________________________________________________

What is claimed is:
 1. A compound of the formula: ##STR121## wherein R₁is S(O)_(n) R₅, CF₃, NR₆ R₇, CO₂ R₈, SO₂ NR₉ R₁₀, ##STR122## OSO₂ R₁₃,CH₂ OR₁₄ or Q; R₂ is S(O)_(m) R₅, CF₃, NR₆ R₇, CO₂ R₈, SO₂ NR₉ R₁₀,##STR123## OSO₂ R₁₃, CH₂ OR₁₄ or Q; R₃ is H, Cl, F, Br, CH₃, OCH₃ or CF₃;R₄ is H or CH₃ ; R₅ is C₁ -C₃ alkyl; R₆ and R₇ are independently CH₃ orCH₂ CH₃ ; R₈ is C₁ -C₃ alkyl, CH₂ CH═CH₂, CH₂ CH₂ Cl or CH₂ CH₂ OCH₃ ;R₉ is CH₃ or OCH₃ ; R₁₀ is C₁ -C₃ alkyl; R₁₁ is H, Cl, Br, F, CH₃ orOCH₃ ; R₁₂ is H or CH₃ ; R₁₃ is C₁ -C₃ alkyl or CF₃ ; R₁₄ is C₁ -C₃alkyl or CF₂ H; n is 0, 1 or 2; m is 0 or 1; ##STR124## W is O, S orNR₁₈ ; W' is O or S; R₁₅, R₁₆, R₁₇ and R₁₈ are independently H or CH₃ ;Q is also ##STR125## R₁₉, R₂₀, R₂₂, R₂₄ and R₂₅ are independently H orCH₃ ; R₂₁ and R₂₃ are independently H, CH₃ or OCH₃ ; Q is also##STR126## R₂₆, R₂₇, R₂₈ R₂₉, R₃₀ and R₃₁ are independently H or CH₃ ; Ais ##STR127## L is O; X₁ is CH₃, OCH₃, Cl or OCF₂ H; and Y₃ is H or CH₃;and agriculturally suitable salts thereof; provided that (a) wheneither one of R₁ or R₂ is CF₃, then the other is also CF₃ ; (b) R₁ andR₂ are not simultaneously CO₂ R₈ ; (c) when either one of R₁ or R₂ isSO₂ NR₉ R₁₀, then the other must not be S(O)_(n) R₅, S(O)_(m) R₅, CH₂OR₁₄ or NR₆ R₇ ; (d) when R₉ is OCH₃, then R₁₀ is CH₃ ; (e) when eitherone of R₁ or R₂ is CO₂ R₈, then the other must not be S(O)_(n) R₅,S(O)_(m) R₅ or NR₆ R₇ ; and (f) the total number of carbon atoms in R₂₆to R₃₁ combined, is equal to or less than four.
 2. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected postemergence or preemergence an effectiveamount of a compound of claim
 1. 3. An agriculturally suitablecomposition for controlling the growth of undesired vegetationcomprising an effective amount of a compound of claim 1 and at least oneof the following: surfactant, solid or liquid diluent.